Category: 6136-93-2

Murakami, Teiichi; Otsuka, Masami; Ohno, Masaji published the artcile< An efficient synthesis of 5-diethoxymethylimidazole-4-carboxylate: a potential precursor for various imidazole derivatives>, Name: 2,2-Diethoxyacetonitrile, the main research area is ethoxymethylimidazolecarboxylate; imidazolecarboxylate diethoxymethyl; cycloaddition ethoxyacetonitrile methyl isocyanoacetate; nitrile cycloaddition methyl isocyanoacetate.

The title imidazolecarboxylate I [R = CH(OEt)2] was prepared in 82% yield by cycloaddition reaction of (EtO)2CHCN with CNCH2CO2Me in diglyme containing KH at 0-70° for 5 h. I [R = (MeO)3C, Ph, pyridyl, furyl] were similarly prepared in 13-85% yield.

Tetrahedron Letters published new progress about Cycloaddition reaction. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Name: 2,2-Diethoxyacetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Fache, F.; Cros, F.; Piva, O.; Lefebvre, F. published the artcile< Easy access to 2-alkyl and 2-arylthiazolines using a modified heteropolyacid catalysis: application to the synthesis of bacillamide A>, Synthetic Route of 6136-93-2, the main research area is thiazoline preparation microwave irradiation; aminothiol nitrile cyclization phosphotungstic acid catalyst.

A straightforward access to 2-alkyl and 2-arylthiazolines by condensation of β-aminothiols on nitriles, catalyzed by phosphotungstic acid (2%) under microwave irradiation, is described. This method has been directly applied to a short and efficient synthesis of bacillamide A.

Synthetic Communications published new progress about Heterocyclic compounds Role: SPN (Synthetic Preparation), PREP (Preparation). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Synthetic Route of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Hora, J. published the artcile< The synthesis of bis-endo-2-(hydroxymethyl)-5-(4-imidazolylmethyl)bicyclo[2.2.2]octane and the corresponding cyclohexane analog>, Product Details of C6H11NO2, the main research area is bicyclooctane imidazolylmethyl; cyclohexane imidazolylmethyl; imidazole bicyclooctanyl; cyclization aminoacetal.

The imidazolylbicyclooctane I was prepared in 9 steps by cyclization of 3,4-dihydrobenzoic acid with H2C:CHCO2Me and conversion of the II (R = CO2H, R1 = CO2Me) to II (R = tetrahydropyranyl, R1 = CH2Br) which was treated with Mg and (EtO)2CHCN, followed by reduction formylation, cyclization with HCONH2. 3-Oxabicyclononane was treated with MeCOCl and the cis-1-(chloromethyl)-4-(hydroxymethyl)cyclohexane similarly converted to III.

Recueil des Travaux Chimiques des Pays-Bas published new progress about Cyclization. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Product Details of C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Fare, Fiorenza; Dei Cas, Michele; Arnoldi, Sebastiano; Casagni, Eleonora; Visconti, Giacomo Luca; Parnisari, Giulia; Bolchi, Cristiano; Pallavicini, Marco; Gambaro, Veniero; Roda, Gabriella published the artcile< Determination of Methyldibromoglutaronitrile (MDBGN) in Skin Care Products by Gaschromatography-Mass Spectrometry Employing an Enhanced Matrix Removal (EMR) Lipid Clean-Up>, HPLC of Formula: 6136-93-2, the main research area is methyldibromoglutaronitrile skin care product gas chromatog mass spectrometry.

A new application of QuEChERS extraction followed by EMR-lipid cleanup and GC-MS anal. is proposed for skin care products. Method is applied to determine MDBGN, a preservative frequently used in cosmetic products before being banned for its allergic reactions. New validated procedure consists in extractingcosmetic products with acetonitrile, removing the lipid matrix and then water and solid particles from organic mixture by two dSPE in sequence and, lastly, analyzing extracts in GC-MS. Compared to classic liquid-liquid extraction with chloroform,method has superior features in terms of applicability to cosmetics, ease of use, working times optimization and, above all, reduction of anal. interfering lipidic constituents. Use of EMR-Lipid dSPE system followed by GC-MS anal. allows to trace and quantify a minimal amount of a banned preservative, MDBGN, in so-called “”complex”” matrixes, such as cosmetic creams. This system shows following advantages: much simpler use, as system provides tubes already packaged with clean-up phase, optimization of working times, and noticeable reduction of extraction impurities allowing cleaner extracts to be obtained. A new application of QuEChERS extraction followed by enhanced matrix removal-lipid cleanup and GC-MS anal. is proposed for skin care products. Compared to classic liquid-liquid extraction with chloroform (upper part),method has superior features in terms of applicability to cosmetics, ease of use, working times optimization and, above all, reduction of anal. interfering lipidic constituents .

European Journal of Lipid Science and Technology published new progress about Chamomile. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, HPLC of Formula: 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Amini, Mohsen; Golabchifar, Ali A.; Dehpour, Ahmad R.; Pirali, Hamedani M.; Shafiee, Abbas published the artcile< Synthesis and calcium channel antagonist activity of new 1,4-dihydropyridine derivatives containing dichloroimidazolyl substituents>, Name: 2,2-Diethoxyacetonitrile, the main research area is calcium channel antagonist dihydropyridine derivative structure design lipophilicity; cardiovascular calcium channel antagonist dihydropyridine structure design.

A group of dialkyl, dicycloalkyl and diaryl ester analogs of nifedipine (CAS 21829-25-4), in which the ortho-nitrophenyl group at position 4 is replaced by a 4,5-dichloroimidazolyl substituent, were synthesized and evaluated as calcium channel antagonists using the high K+ contraction of guinea-pig ileal longitudinal smooth muscle. The results for the sym. esters in alkyl esters series showed that increasing the length of the methylene chain in C3 and C5 ester substituents (from n = 0 to n = 2) increased the activity. When increasing of the length was accompanied by increase of the hindrance, the activity decreased. In the unsym. diester series, the results showed when R1 is a small substituent (R1 = Me), increasing of the lipophilic property in R2 substituent increases the activity if this high lipophilicity is not accompanied by steric hindrance. The results demonstrate that in the unsym. series, several compounds (benzyl Me, benzyl iso-Pr and cyclohexyl ethyl) had activity similar to that of the reference drug nifedipine. In sym. diesters compounds, the most active compound was the diphenethyl ester derivative being more active than nifedipine. These structure-activity data indicate that the 4-(4,5-dichloroimidazolyl) moiety is the bioisoester of 3-nitrophenyl and 2,3-dichlorophenyl moieties.

Arzneimittel-Forschung published new progress about Calcium channel blockers. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Name: 2,2-Diethoxyacetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kelly, T. Ross; Bell, Stephen H.; Ohashi, Naohito; Armstrong-Chong, Rosemary J. published the artcile< Synthesis of (±)-fredericamycin A>, HPLC of Formula: 6136-93-2, the main research area is fredericamycin A total synthesis.

The synthesis of (±)-Fredericamycin A (I) and supporting studies are reported. In model studies the parent spiro system was constructed from C6H4(CO2Me)2-o and indene. Synthons for the upper and lower units of I were prepared, followed by regiospecific coupling and elaboration of the resulting product into I.

Journal of the American Chemical Society published new progress about 6136-93-2. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, HPLC of Formula: 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sanchez-Viesca, F.; Gomez, Maria R.; Berros, Martha published the artcile< An anomalous Houben-Hoesch reaction and some applications in arylation reactions>, Recommanded Product: 2,2-Diethoxyacetonitrile, the main research area is anomalous Houben Hoesch reaction methoxybenzene arylation application.

α,α-Dichloro-2,4,5-trimethoxyacetophenone (1a), prepared via a Houben-Hoesch reaction between 1,2,4-trimethoxybenzene and dichloroacetonitrile, was very unreactive, failing to react with NaOAc, methoxide and ethoxide. Attempted preparation of α,α-diethoxy-2,4,5-trimethoxyacetophenone by Houben-Hoesch reaction of 1,2,4-trimethoxybenzene with diethoxyacetonitrile gave tris(2,4,5-trimethoxyphenyl)methane instead. Reaction of 1,2,4-trimethoxybenzene with diethoxyacetonitrile under Houben-Hoesch conditions gave 2,2-bis(2,4,5-trimethoxyphenyl)acetamide. 2,2-Dichloro-1-methoxy-1-(2,4,5-trimethoxyphenyl)ethane (preparation described) could be arylated by 1,2,4-trimethoxybenzene and 2,4-dimethoxychlorobenzene to give 2,2-dichloro-1,1-bis(2,4,5-trimethoxyphenyl)ethane and 2,2-dichloro-1-(5-chloro-2,4-dimethoxyphenyl)-1-(2,4,5-trimethoxyphenyl)ethane. Reactions of 1,2,4-trimethoxybenzene with RCH2CN (R = EtO, MeO) under Houben-Hoesch conditions gave 2,4,5-trimethoxyphenacyl chloride (unexpectedly) and α-methoxy-2,4,5-trimethoxyacetophenone, resp.

Organic Preparations and Procedures International published new progress about Hoesch reaction. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Recommanded Product: 2,2-Diethoxyacetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Meerwein, Hans; Hederich, Volker; Morschel, Hans; Wunderlich, Klaus published the artcile< Intermolecular anion transfer during organic reactions>, Formula: C6H11NO2, the main research area is .

A class of reaction mechanisms, RA + R’+ → R’A + R+, is considered, where R+ is the more stable carbonium ion, A = hydride, cyanide, or alkoxide; isolation of the R+ salts is attempted. Ph3C+ is chosen as R’+ and prepared by stirring 44.5 g. BF3-EtOAc, b13 49-51°, into 61 g. Ph3COEt in 170 cc. EtOAc with exclusion of H2O and alc., separation of Ph3CBF3 (I) by filtering after 24 hrs., and washing with low-boiling petroleum; total yield after recovery of 2nd crop 90%, m. 197-8°. Addition of 7.4 g. 1,3-dioxolane to 16.5 g. I in 60 cc. liquid SO2 under reflux (dry ice condenser) results in hydride transfer and, after evaporation and treatment with CH2Cl2 and Et2O, isolation of 88.5% 1,3-dioxolenium fluoborate, m. 83°; β-iodoethyl formate b15 65-70°, prepared with NaI in MeCN. From the CH2Cl2 washings, 58% Ph3CH, m. 90.5-1.5°, is isolated. Similarly, 2-methyl-1,3-dioxolane, the 2-Ph compound (II), and the 2,4,4,5,5-Me5 compound yield, resp., 84, 83, and 77% Ph3CH, and 69, 100, and 76% (m. 150-2°) dioxolenium fluoborates. In order to substitute for I the nonexistent Et +, 9.5 g. (Et3O) (BF4) and 9 g. II is heated to 40°, 81% Et2O distilled, and 50% II-BF4 salt and C2H6 isolated. Another H- donor is (PhCH2)3N, reacting with I in MeCN at 40-50° to yield 84% Ph3CH and 94% benzylidenedibenzylimonium fluoborate, m. 132-4°, hydrolyzed in hot 30% NaOH to (PhCH2)2NH. Cyanide transfer occurs by cooling 5 g. 2-cyano-2-methyl-1,3-dioxolane (III) in 25 cc. MeCN with 14.5 g. I, filtering off after 1 hr. 6.5 g. Ph3CCN, m. 128.6-29° (total yield 82%), and adding Et2O to isolate 59% 2-methyldioxolenium fluoborate (IV), m. 162-4°, and recover more Ph3CCN from the filtrate. III reacts with (EtO)2CHBF4, m. 20°, in CH2Cl2 to yield 88% IV and 81% (EtO)2CHCN, b760 163-4°, b15 58-9.5°, n20D 1.3978. Alkoxide transfer is reversible and usually more rapid than hydride transfer. Camphor diethyl acetal, b10 99.5-101°, (18 g.) added to 16.5 g. I in 25 cc. MeCN precipitates 95% O-ethylcamphoroxonium fluoborate, decomposed at 104-5%, isolated by washing with Et2O; 90% Ph3COEt (V), m. 82°, is obtained by evaporation of the filtrate. Similar high-yield reactions of ROEt with I or HC(OEt)2BF4 (VI) give the R salt and V or HC(OEt)3 for R = O.CH2.CH2.O.CMe (both I and VI), C(OEt)3 (both I and VI), O.CMe2.CMe2.O.CH (I only), O.CHMe.CHMe.O.CH (I only), HC(OEt)2 (Ph3CSbCl6), Me2NCHOEt [Ph3CSbCl6, VI, and HC(OEt)2SbCl6]. V is cleaved by R’BF4 (R’ = 2-methyl-, 4,5-dimethyl-, or 2,4,4,5,5-pentamethyldioxolenium) with isolation of Ph3CH and AcH. With ROEt (R = O.CH2.CH2.CH), I in CH2Cl2 yields 88% RBF4 and 95% Ph3CH, but in MeCN the same reaction produces 91% Ph3COCH2CH2COCPh3 (VII), m. 188-9° (MeCOEt), and by attack on O and ring cleavage, some RBF4, and VI. When not isolated, VII decompose to Ph3CH. RBF4 in turn reacts with V in MeCN to yield 33% VII, and VII with VI in CH2Cl2 to yield 75% RBF4. From 13.2 g. I in 20-25 cc. dry CH2Cl2, treated with 8.5 g. RNMe2 (R = O.CH2.CH2.O.CMe), b. 142°, with cooling and stirring 30 min. after slow addition, Et2O precipitates [RN(CPh3)Me2]BF4, stable, m. 170°; the iodide, obtained by treatment with NaI in MeCN, decompose at 110° to 88.5% AcNMe2, b30 76-7°, recovered by distillation, and 78.6% ICH2CH2OCPh3, m. 136-7°, obtained by crystallization of the residue from alc. or MeCN. The ether is obtained independently for comparison from Ph3CH and HO(CH2)2Br in C5H5N via the Br compound, m. 126-7%, and refluxing the latter with NaI in MeCN. The mechanisms are discussed. The new (OCMe2CMe2OCH)BF4 m. 110-12° and (Me2NCHOEt)SbCl6 m. 156-8°.

Annalen der Chemie, Justus Liebigs published new progress about Anions. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Formula: C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Schaefer, Fred C.; Peters, Grace A. published the artcile< Base-catalyzed reaction of nitriles with alcohols. A convenient route to imidates and amidine salts>, Electric Literature of 6136-93-2, the main research area is .

The base-catalyzed reaction of nitriles with alcs. to form imidates was estimated as an attractive preparative method which was useful for a wide variety of electroneg. substituted aliphatic and aromatic nitriles. This reaction was used as the basis for a convenient procedure for the preparation of amidine salts. In general, 0.100 mole of the purified nitrile was mixed with MeOH, 0.010 mole NaOMe added, the solution diluted to 100 ml. at 25°, and liquors withdrawn at intervals, added to 0.100N HCl, and back titrated potentiometrically. In most cases, substantial conversion occurred within 0.5 hr. and the reaction was close to equilibrium in less than 24 hrs. The following results of comparative reactions were obtained under the standard conditions (nitrile, time in hrs., and % conversion to imidate given): NCCMe2CMe2CN, 22, 1; NC(CH2)4CN, 24, 1.5; MeCN, 2, 2; PhCH2CN, 24, 12; Et2NCH2CN, 48, 22; NC(CH2)2CN, 24, 69; BuOCH2OCHMeCN, 96, 86; [Et3NCH2CN]Cl, 48, 76; Me3COCH2CN, 30, 91; CH2:CClCN, 25, 90; MeCHClCN, 0.5, 91; CH2ClCN, 0.5, 93; (EtO)2CHCN, 1, 95; p-MeOC6H4CN, 96, 15; PhCN, 20, 20; p-ClC6H4CN, 48, 45; p-O2NC6H4CN, 8, 83; m-O2NC6H4CN, 4, 86; p-C6H4(CN)2, 7, 108; 3-(C5H4N)CN, 24, 71; (2-C5H4N)CN, 2, 97; Me2NCN, 24, 100 Et2NCN, 144, 100. Some nitriles gave no apparent imidate under the standard conditions. Titration of acid-hydrolyzed aliquots was carried out potentiometrically with 2 end points being observed (at pH 7 and 3.5). Addnl. experiments were carried out with p-O2NC6H4CN at different catalyst concentrations At 25° and 0.95M, the following equilibrium conversions were obtained: 0.050M NaOMe, 83%; 0.10M NaOMe, 81%; 0.20M NaOMe, 78%. (Effect of temperature). In 7 hrs. at 25°, 100 cc. MeOH containing 0.010 mole NaOMe dissolved 5.1 g. terephthalonitrile. Titration showed the presence of 0.042 mole of imidate. When the reaction mixture was heated 3 hrs. at 65°, the imidate content dropped to 0.025 mole; conversion 62.5%. In a similar experiment, it was shown that conversion to imidate in 0.04 M solution p-nitrobenzonitrile decreased from 80 to 50% on heating from 25° to 65°. The expected higher conversion at temperatures below 25° was noted with M p-chlorobenzonitrile in MeOH. When inert solvents were used the equilibrium conversions at 25° of p-nitrobenzonitrile were 13% in 90% C6H6 and 15% in 80% dioxane. With terephthalonitrile in 50% PhNO2, conversion was 19%; in 80% 2-methoxyethanol, 26%. With 2,2-diethoxyacetonitrile (I) as the standard reagent, a number of alcs. were studied with equilibria determined at 25°. The following results were obtained (R of ROH, and equilibrium conversion in % given): Me, 95; Me, 95; Me (3% H2O), 91; Et, 89; Pr, 82; Bu, 78; iso-Bu, 78; iso-Pr, 63. p-Nitrobenzonitrile (M) with anhydrous alc. containing 0.01M NaOMe gave 78% imidate at 25°. I (studied for reaction rate as a function of catalyst concentration) gave the following results (molar concentration of catalyst, k in min.-1, and k’ in l. mole-1 min.-1 given): 0.10, 0.098, 0.98; 0.071, 0.071, 0.99; 0.050, 0.048, 0.96. When KCN in MeOH was used as a catalyst, a clear solution was obtained after 120 hrs. with p-nitrobenzonitrile and in an addnl. 24 hrs. equilibrium was reached at 79% conversion. Cyanomethyltrimethylammonium chloride reacted normally with MeOH and KCN, although MeO- caused degradation. Isopropoxyacetonitrile (15 g.) and 0.5 g. NaOMe in 50 cc. MeOH was kept overnight at room temperature; titration indicated an 81% conversion and isolation gave 13.2 g. Me 2-isopropoxyacetimidate, b2 32-7°. 2-Cyanopyridine (26 g.) and 1.35 g. NaOMe in 225 cc. MeOH kept overnight at room temperature gave 31.4 g. Me pyridine-2-carboximidate, b23 118-22°. p-Nitrobenzonitrile (35 g.) and 100 cc. MeOH containing 1 g. NaOMe refluxed 4 hrs. gave 13.3 g. unchanged nitrile and 21.7 g. Me p-nitrobenzimidate, m. 75°, contaminated with some Me p-nitrobenzoate and p-nitrobenzamide. 2-Chloropropionitrile (65 g.) in 200 cc. alc. and 2.2 g. NaOMe kept 45 min. at 25° gave 53 g. Et 2-chloropropionimidate, b60 70-5°. Several amidine salts were prepared A MeOH solution of an imidate was treated with NH4Cl, the mixture stirred a few hrs. (reaction time 1-24 hrs.), solvent removed, and the product extracted with Et2O and recrystallized The following RC:NHNH2.HCl were thus prepared (R, molar concentration of original nitrile, molar concentration NaOMe catalyst, % yield, and m.p. given): CH2Cl, 2.5, 0.07, 96, 95-9°; MeCHCl, 3.1, 0.20, 73, 130-1°; Me3COCH2, 1.00, 0.10, 78, 157-9°; m-O2NC6H4, 1.00, 0.10, 80, 250-2°; p-O2NC6H4, 0.05, 0.050, 78, 285-7°; 3-C6H4N, 1.00, 0.10, 192-4°; 2-C5H4N, 1.00, 0.10, 95, 149-51°. In other work, excellent yields of amidine thiocyanates, acetates, and bromides were obtained by use of the appropriate ammonium salt. Terephthalonitrile (10 g.) and 100 cc. MeOH containing 0.50 g. NaOMe refluxed 2.5 hrs. and the hot solution added to 150 cc. ice H2O containing 12 cc. 12N HCl, kept overnight, and the product separated gave 61% Me p-cyanobenzoate, m. 59-61°. Di-Me terephthalate was expected to arise from the diimidate present, but could conceivably have been dissolved in the discarded aqueous MeOH.

Journal of Organic Chemistry published new progress about Alcohols Role: USES (Uses). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Electric Literature of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Boehme, Horst; Neidlein, Richard published the artcile< The cleavage of orthocarboxylic acid esters with acyl halides and acyl cyanides>, Name: 2,2-Diethoxyacetonitrile, the main research area is .

HC(OPh)3 (I) with acyl halides yields the corresponding carboxylic acid Ph esters and (PhO)2CHCl (II) which reacts readily with PhSH and with Me2NH. Orthocarboxylic acid esters, orthocarbonates, and acetals are cleaved by AcCN with the formation of carboxylic acid esters and derivatives of (EtO)2CHCN (III). I (2.9 g.) and 0.8 g. AcCl kept 5 days at room temperature under N, filtered, and distilled gave 1.1 g. PhOAc, b0.15 40-52°, n20D 1.5012, 1.4 g. II, b0.15 128-30°, and unchanged I, b0.15 175-7°, m. 72-3°. CCl3COCl (1.8 g.) added with cooling under N to 2.9 g. I, kept 2 hrs. at room temperature, and worked up gave 1.9 g. CCl3CO2Ph, b0.2 114-17°, 1.6 g. II, b0.2 128-30°, and 0.8 g. I, b0.2 178-80°, m. 71-2°. II (2.3 g.) in 10 cc. absolute Et2O added dropwise with stirring to 1.1 g. LiAlH4 in 20 cc. Et2O, refluxed briefly, and worked up yielded 1.8 g. (PhO)2CH2, b13 164-5°. II (4.7 g.) in 10 cc. dry Et2O treated with stirring at -50° with 1.8 g. dry Me2NH in a dry stream of N, kept 3 hrs. at -50°, warmed to room temperature, filtered, and distilled gave 0.9 g. (PhO)2CHNMe2, b0·.01 46-8°, and 2.8 g. I. II (2.3 g.) in 30 cc. dry Et2O treated successively with 1.0 g. C5H5N in 8 cc. dry Et2O and 1.1 g. PhSH, refrigerated 30 days, decanted, and worked up yielded 1.3 g. PhSCH(OPh)2, m. 49-50° (Et2O). p-MeOC6H4CH(OEt)2 (10.5 g.) added dropwise at -60° to 6.2 g. AcBr under dry N, warmed to 0°, diluted with 100 cc. absolute petr. ether at room temperature, cooled to -60°, and filtered gave p-MeOC6H4CHBrOEt (IV) which decompose with fuming and elimination of p-MeOC6H4CHO (phenylhydrazone m. 120.5°; semicarbazone m. 208.5°). IV (1.2 g.) and 0.6 g. PhSH in 50 cc. petr. ether treated with cooling with 0.4 g. C5H5N, kept 2 hrs. at room temperature, filtered, washed, and evaporated yielded 0.5 g. p-MeOC6H4CH(SPh)OEt, m. 80-1° (hexane). IV (2.0 g.) in 70 cc. dry petr. ether treated with stirring with 3 cc. 0.01M PhMgBr, refluxed 2 hrs., and worked up gave p-MeOC6H4CH(OEt)Ph, yellowish oil, b0.01 98-100°. AcCN (3.5 g.) added dropwise to 7.4 g. HC(OEt)3, heated 20 hrs. at 80° under N, and distilled gave 0.8 g. HCO2Et, b. 52-7°, n20D 1.3587, 3.6 g. EtOAc, b. 74-5°, n20D 1.3713, and 3.3 g. III, b12 56-8°, n25D 1.3934. PhC(OEt)3 (11.2 g.) and 3.5 g. AcCN heated 50 hrs. at 90° in a sealed tube gave 2.9 g. EtOAc, 0.8 g. AcOC(CN)2Me (V), b15 94-104°, and 4.6 g. (EtO)2C(CN)Ph, b15 126-30°, n20D 1.4815. C(OEt)4 (9.6 g.) and 3.5 g. AcCN heated 48 hrs. at 80-90° gave 3.6 g. EtOAc, some unchanged C(OEt)4, b13 46-8°, n20D 1.3940, and 3.2 g. (EtO)3CCN, b13 58-60°, n20D 1.3995. MeCH(OEt)2 (5.9 g.) and 3.5 g. AcCN heated 16 hrs. at 90° gave 1.4 g. EtOAc, unchanged AcCN, 0.5 g. MeCH(OEt)CN, b10 30-1°, n20D 1.3875, and 1.4 g. V, b11 101-2°, m. 67-8°.

Chemische Berichte published new progress about Esters. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Name: 2,2-Diethoxyacetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts