Category: nitriles-buliding-blocks

Some common heterocyclic compound, 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, molecular formula is C9H6BrNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C9H6BrNO

General procedure: Method C: Almac CRED (200 mg) andNADP or NAD (10 mg) were measured into a 250 mL roundbottomedflask then dissolved in 0.1 M potassium phosphate buffer(pH 7, ca. 50 mL). IPA (7 mL) was added, followed by a solutionof ketone (900-1700 mg) in DMSO (2.5-5 mL, depending on solubility).This was stirred at 35 C under 500 mbar reduced pressureto aid removal of acetone formed by IPA oxidation. Standardwork-up procedure: The pH of the reaction mixture was adjustedif necessary (basic or acidic depending on estimated pKa of alcoholproduct) with either 1 M NaOH or 1 M HCl. The reaction mixturewas then extracted with MTBE (3 100 mL).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4592-94-3, its application will become more common.

Reference:
Article; Rowan, Andrew S.; Moody, Thomas S.; Howard, Roger M.; Underwood, Toby J.; Miskelly, Iain R.; He, Yanan; Wang, Bo; Tetrahedron Asymmetry; vol. 24; 21-22; (2013); p. 1369 – 1381;,
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Electric Literature of 6136-93-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 6136-93-2, name is 2,2-Diethoxyacetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

2,2-Diethoxyacetonitrile 1 (25 g, 193 mmol) was mixed with (NH4)25 (40 mL, 265 mmol, 45% aq. solution in) in 300 mL of methanol (MeOH) at room temperature (RT). After keeping the reaction mixture overnight, it was concentrated under vacuum and the residue was taken up in ethyl acetate (EtOAc). The EtOAc solution was washed with saturatedNaHCO solution then brine and dried over anhydrous Na2504. The EtOAc was evaporated to give thioamide 2 (26 g, 159 mmol, 82%) as a white solid. ?H NMR (400 MHz, CDC13) oe 5.01 (s, 1H), 3.67 (m, 4H), 1.22 (t, J=7.2 Hz, 6H).

The chemical industry reduces the impact on the environment during synthesis 2,2-Diethoxyacetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; E. R. SQUIBB & SONS, L.L.C.; Cheng, Heng; Gangwar, Sanjeev; Cong, Qiang; (82 pag.)US9226974; (2016); B2;,
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Synthetic Route of 2941-29-9, A common heterocyclic compound, 2941-29-9, name is Cyclopentanone-2-carbonitrile, molecular formula is C6H7NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[00688] Intermediate 74e: benzyl N-{4-[(2-cyanocyclopent-1 -en-I -yI)(cyanomethyl)am ino]-2- (trifluoromethoxy)phenyl}carbamate[00689] p-Toluenesulfonic acid monohydrate (0.08g, 0.43mmol) was added to a solution of benzylN-[4-(cyanomethylamino)-2-(trifluoromethoxy)phenyl]carbamate (1 .57g, 4.3mmol) and IntermediateI (0.52g, 4.73mmol) in toluene (4OmL). The resulting solution was heated to reflux for 5 hours under Dean-Stark conditions, the mixture was then cooled to room temperature and allowed to stand overnight. The solution was transferred to a separating funnel, washed with sat. aq. NaHCO3 solution (5OmL) and the aqueous washed with EtOAc (3 x 5OmL). The organic layers werecombined, washed with brine (5OmL), dried over Na2504 and the solvent removed in vacuo to give benzyl N-{4-[(2-cyanocyclopent-1 -en-i -yl)(cyanomethyl)amino]-2- (trifluoromethoxy)phenyl}carbamate as a brown oil (2.02g, 4.3mmol, 100percent yield) which was used as is in the next step without further purification.MS Method 2: RT: 1.90 mi m/z = 457.2 [M+H]

The synthetic route of 2941-29-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4110-35-4, name is 3,5-Dinitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H3N3O4

a. 3,5-Diaminobenzonitrile To a solution of 210 grams of stannous chloride dihydrate in 590 ml. of concentrated hydrochloric acid is added portionwise 25 grams of 3,5-dinitrobenzonitrile. The mixture is stirred for 3 hours at room temperature, then cooled to 0 in an ice-salt bath and a cold 50% sodium hydroxide solution added to the mixture until the mixture is strongly basic. During the addition the temperature is kept below 5. The mixture is extracted with methylene chloride and the solvent removed. There is obtained 2.25 grams of material melting at 185-8. Recrystallization from ethanol raises the melting point to 188-9. Analysis Calcd. for: C7 H7 N3 C, 63.14; H, 5.30; N, 31.56. Found: C, 62.87; H, 5.19; N, 31.72.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4110-35-4.

Reference:
Patent; The Upjohn Company; US3993679; (1976); A;,
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Reference of 6575-13-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6575-13-9 name is 2,6-Dimethylbenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A 10 mL round-bottomed flask was charged with the appropriate nitrile 2 (0.50 mmol), arylboronic acid 1(0.60 mmol), CuBr2 (6 mg, 5mol%), t-BuOK (168 mg, 1.50 mmol), and t-BuOH (3.0 mL), and the mixture was stirred at r.t. until the reaction was complete (TLC). H2O (4.0 mL) was added, and the mixture was extracted with EtOAc (3 ×10 mL). The combined organic layers were washed twice with H2O,dried (Na2SO4), and concentrated to give a residue that was purified by column chromatography (silica gel, PE-EtOAc).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dimethylbenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Qiao, Yan; Li, Gaoqiang; Liu, Sha; Yangkai, Yujie; Tu, Jingxuan; Xu, Feng; Synthesis; vol. 49; 8; (2017); p. 1834 – 1838;,
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Some common heterocyclic compound, 64695-82-5, name is 2-Bromo-4,5-difluorobenzonitrile, molecular formula is C7H2BrF2N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C7H2BrF2N

A solution of 2-bromo-4,5-difluorobenzonitrile (218 mg, 1.00 mmol), (R)-2-amino- 3-cyclopropylpropanamide (188 mg, 1.14 mmol) and DIEA (0.600 mL, 3.45 mmol) in DMSO (3 mL) was stirred at 120 C for 18 h. Water and EtOAc were added. The organic phase was separated, washed with water, dried over Na2S04, concentrated in vacuo to give (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-cyclopropylpropanamide (326 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64695-82-5, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong, J.; SONG, Yonghong; XU, Qing; KANE, Brian; BAUER, Shawn, M.; PANDEY, Anjali; WO2012/61418; (2012); A2;,
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Related Products of 59997-51-2, These common heterocyclic compound, 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To an aqueous solution of sodium hydroxide solution (0.84 g,21 mmol) in water (10 mL), pivaloylacetonitrile (1.25 g, 10 mmol) and hydroxylamine hydrochloride(0.76 g, 11 mmol) were added. The resulting solution was stirred at 50 C for 3 h. The reaction mixture was cooled and the resultant white crystalline solid was filtered, washed with water and dried to provide compound 25r as a white crystalline solid (1.23 g, yield 88%).

Statistics shows that 4,4-Dimethyl-3-oxopentanenitrile is playing an increasingly important role. we look forward to future research findings about 59997-51-2.

Reference:
Article; Li, Xingzhou; Zhou, Xinming; Zhang, Jing; Wang, Lili; Long, Long; Zheng, Zhibing; Li, Song; Zhong, Wu; Molecules; vol. 19; 2; (2014); p. 2004 – 2028;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 53312-77-9, name is 2-Amino-3-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Amino-3-chlorobenzonitrile

To a solution of 2-amino-3-chlorobenzonitrile (5.0 g, 32.9 mmol) in dry DMF (60 mL) was added NaH (1.97 g, 60%, 49.3 mmol) at 0 C. Then, the mixture was stirred at 0 C for 15 min. Mel (4.67 g, 32.9 mmol) was added and the mixture was stirred at rt for 2 hrs. The reaction solution was quenched with saturated NH4C1 solution, diluted with EtOAc (200 mL), washed with H20 (2x) and brine (2x), dried (Na2S04), filtered, and concentrated. The residue was purified by silica gel column chromatography (EtOAc/PE=0~5%) to give 3-chloro-2- (methylamino)benzonitrile (4.8 g, 88%) as a white solid. ESI-MS (EI+, m/z): 167.0 [M+1]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 53312-77-9.

Reference:
Patent; DISCOVERYBIOMED, INC.; SCHWIEBERT, Erik; STREIFF, John; DIXON, John; GAO, Hongwu; WO2014/152213; (2014); A2;,
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These common heterocyclic compound, 72291-30-6, name is Methyl 2-cyano-2-methylpropanoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: Methyl 2-cyano-2-methylpropanoate

50L adding glass cauldron 25L methanol, add 2.20 kg potassium hydroxide (39.4mol), stirring then after cooling to room temperature, dropping 5.00kg2-cyano-2-methyl propane acid methyl ester (39.4mol), stirring reaction after dropping 2h; reaction the fluid turns on lathe dry, solid with a small amount of anhydrous ethanol after washing, 50 C drying, obtain 5.53kg2-cyano-2-methyl propane acid potassium, molar yield 93%.

The synthetic route of Methyl 2-cyano-2-methylpropanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hefei Leaf Biotechnology Limited; Deng, Jin; Wang, Peng; Fu, Yao; Ding, Fan; Xu, Qiang; Xu, Hai; Yu, Sanxi; Ding, Feijiao; Wu, Jiangjiang; Huang, Ligang; Xu, Shengchun; (8 pag.)CN105541594; (2016); A;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 654-70-6 as follows. Quality Control of 4-Cyano-3-trifluoromethylaniline

4-cyano-3-trifluoromethyl-aniline is reacted with propene-2-sulfonyl chloride (51), and subjected to epoxidation followed by opening of the epoxide ring with p-CN-phenol in the presence of potassium carbonate to yield compound V, as presented in Figure 1 C.

According to the analysis of related databases, 654-70-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OSURF (OHIO STATE UNIVERSITY RESEARCH FOUNDATION); UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; WO2008/11072; (2008); A2;,
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