Month: July 2021

Electric Literature of 98730-77-9,Some common heterocyclic compound, 98730-77-9, name is 1-(Hydroxymethyl)cyclopropanecarbonitrile, molecular formula is C5H7NO, 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.

PPh3 (6.48 g, 24.71 mmol) and imidazole (1.682 g, 24.71 mmol) were dissolved in DCM (35 ml) and stirred at 0C. After 5 minutes, iodine (5.75 g, 22.65 mmol) was added. The resulting suspension was stirred at the same temperature for another 30 min. The solution of 1- (hydroxymethyl)cyclopropanecarbonitrile (2 g, 20.59 mmol) in 2 ml of DCM was added to the reaction mixture. The resulting mixture was then stirred at RT for 2 h, after which it was diluted with 20 ml water and 30 ml of satd. Na2S2O3 solution. About 50 ml of ether was added to the flask. The organics were extracted twice using 50 ml of ether, separated and dried over anhydrous MgSO4. The solids were filtered out, and the filtrate was carefully concentrated in vacuo and then directly loaded on a silica gel column and eluted with 0-30% EtOAc in hexanes to afford the title compound.1H NMR (CDCl3, 5000+]^^^^3.18 (s, 2H), 1.16-1.20 (m, 2H), 0.99-1.08 (m, 2H).

The synthetic route of 98730-77-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHEN, Dong-Ming; KUANG, Rongze; KUMAR, Puneet; DUFFY, Joseph, L.; ZHU, Cheng; ALI, Amjad; YANG, Meng; DEBENHAM, John, S.; (124 pag.)WO2018/39094; (2018); A1;,
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These common heterocyclic compound, 49674-16-0, name is 5-Amino-3-bromobenzonitrile, 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. Quality Control of 5-Amino-3-bromobenzonitrile

To a stirring of 965 mg (4.90 mmol) of 3-amino-5-bromobenzonitrile in 15 mL of CH2Cl2 was added 1.27 g (5.09 mmol) of N-(benzyloxycarbonyloxy)succinimide (followed by 5 mL of CH2Cl2), and 1.5 mL (10.8 mmol) of Et3N. After 27 h, the solution was concentrated and 10 mL of 10% citric acid and EtOAc were added. The layers were separated, and the organic layer was washed with 10 rnL of 10% citric acid, 20 rnL of H2O, and 10 rnL of brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (25% EtOAc/hexanes) provided 773 mg of Cbz protected product(benzyl 3-bromo-5-cyanophenylcarbamate) with some impurity.

The synthetic route of 5-Amino-3-bromobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COMENTIS, INC.; PURDUE RESEARCH FOUNDATION; WO2009/42694; (2009); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 185147-07-3, name is 2-Fluoro-3-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-Fluoro-3-methylbenzonitrile

To a mixture of 2-fluoro-3-methylbenzonitrile (4.0 g, 29.6 mmol) and 2H-1 ,2,3- triazole (2.04 g, 29.6 mmol) in DMF (80 ml_) was added potassium carbonate (8.26 g, 59.2 mmol). The resulting mixture was heated to 120 C for 2h. The mixture was cooled, diluted with water and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (S1O2, ethyl acetate/hexanes, gradient 0-50%) to yield the title compound (1 .5 g, 26%). MS (ESI) mass calcd. for Ci0H8N4,184.2; m/z found, 185.1 [M+H]+. 1H NMR (500 MHz, CDCI3): 7.95 (s, 2H), 7.66 (d, J = 7.7, 0.7 Hz, 1 H), 7.59 (d, J = 7.8, 0.6 Hz, 1 H), 7.50 (dd, J = 9.8, 5.7 Hz, 1 H), 2.20 (s, 3H).; Intermediate 36: 3-Methyl-2-(1 H-1 ,2,3-triazol-1 -yl)benzonitrile.The title compound was a byproduct of the synthesis of Intermediate 35 (3.1 g, 56%). MS (ESI) mass calcd. for CioH8N4, 184.2; m/z found, 185.1 [M+H]+. 1 H NMR (500 MHz, CDCI3): 7.94 (d, J = 2.1 Hz, 1 H), 7.87 (d, J = 1 .1 Hz, 1 H), 7.71 – 7.67 (m, 1 H), 7.67 – 7.62 (m, 1 H), 7.56 (dd, J = 9.7, 5.8 Hz, 1 H), 2.17 (s, 3H).

The synthetic route of 185147-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
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Synthetic Route of 13388-75-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 13388-75-5, name is 2-(3,5-Dimethoxyphenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation of (2Z)-2-(3,5-dimethoxyphenyl)-3-{4-[(8-hydroxyoctyl)oxy]phenyl}prop-2-enenitrile 5.0 g (20.0 mmol) of 4-[(8-hydroxyoctyl)oxy]benzaldehyde, 3.5 g (19.8 mmol) of 3,5-(dimethoxyphenyl)acetonitrile are dissolved in 50 mL of propan-2-ol. The solution is heated to 60 C. and 2.0 mL (2.0 mmol) of a one molar solution of tetrabuthylamoniumhydroxyde in methanol are added drop wise. After 2 h at 60 C., the reaction mixture is cooled to 0 C. The precipitate is filtered off, washed with cold propan-2-ol and recristalized in propan-2-ol. 3.5 g of (2Z)-2-(3,5-dimethoxyphenyl)-3-{4-[(8-hydroxyoctyl)oxy]phenyl}prop-2-enenitrile are obtained as a white solid (42% yield). This material proves chromatographically homogenous and displays spectral characteristics consistent with its assigned structure. 1H NMR DMSO-d6 300 MHz: 7.99 (s, 1H), 7.94 (d, 2H), 7.09 (d, 2H), 6.86 (d, 2H), 6.56 (t, 1H), 4.32 (t, 1H), 4.05 (t, 2H), 3.81 (s, 6H), 3.37 (q, 2H), 1.73 (qi, 2H), 1.43-1.29 (m, 10H)

The synthetic route of 2-(3,5-Dimethoxyphenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROLIC AG; Lincker, Frederic; Bury S. Pires, Izabela; Chappellet, Sabrina; Scandiucci De Freitas, Patricia; Ibn-Elhaj, Mohammed; Tang, Qian; Palika, Satish; Hoshino, Masato; Eckert, Jean-Francois; (61 pag.)US9366906; (2016); B2;,
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Synthetic Route of 64248-64-2, 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. 64248-64-2, name is 2,5-Difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of the corresponding 4a-4b (1 equiv.) and 4-amino-3-methylphenol (10 mmol) was stirred 2 h at 90 C in the presence of K2CO3 (4.14g 30 mmol) in DMSO (50 mL). Then the solution was extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), filtered and evaporated to dryness. The product was separated by column chromatography using PE/EA (3:1)as eluent.

The chemical industry reduces the impact on the environment during synthesis 2,5-Difluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhu, Dianxi; Xing, Qifeng; Cao, Ruiyuan; Zhao, Dongmei; Zhong, Wu; Molecules; vol. 21; 5; (2016);,
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Electric Literature of 194853-86-6, A common heterocyclic compound, 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, molecular formula is C8H3F4N, 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.

Potassium carbonate (304 mg, 2 .2 mmol) is dissolved in a minimum amount of water and 4-fluoro-2-trifluoromethylbenzonitrile (378 mg, 2.0 mmol) and trans-4- aminocyclohexanol (460 mg, 4.0 mmol) dissolved in acetonitrile (10 mL) are added. The reaction is then heated at 800C for 3 days. After cooling to room temperature, the mixture is concentrated under reduced pressure, is taken up in ethyl acetate (15 mL) and washed with saturated aqueous ammonium chloride (2 x 10 mL) followed by water (10 mL). The organic phase is collected and dried over sodium sulphate, filtered and concentrated under reduced pressure. The desired product is isolated as a colourless solid (80% yield).

The synthetic route of 194853-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INTERVET INTERNATIONAL B.V.; CHASSAING, Christophe Pierre Alain; MEYER, Thorsten; WO2010/146083; (2010); A1;,
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Application of 621-50-1, 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. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of nitrobenzene acetic acid (1 g, 5.52 mmoles), 1.66 mL OF SOC12, 10 mL dry CHC13 was refluxed for 14 hours. CHC13 and excess thionyl chlorid were removed in vacuo, and the residue was evaporated twice with 25 mL of toluene to remove traces of thionyl chlorid. The residue was taken into 10 mL of toluene and 30 mL of cold concentrated ammonium hydroxyde were added. The white solid formed was collected and dried with etanol in vacuo. Yield: 79 %. ‘H NMR (DMSO-d6, 300MHZ) 8 : 8.14 (M, 2H), 7.71 (M, 2H), 7.06 (brs, 2H), 3.58 (s, 2H). 2- (3-NITROPHENYL) acetamide was added with 10 mL of POC13 and the mixture was heated at reflux for 2 hours. After cooling, the mixture was poured into ice, basified with NA2CO3 and extracted with CH2C12. The organic layer was dried over NA2S04, filtered and evaporated. Purified by flash chromatography on silica gel CH2C12. Yield : 41% H NMR (CDC13,300 MHz) 5 : 8. 14 (M, 2H), 7.69 (d, 1H, J = 8HZ), 7.56 (M, 1H), 3.88 (s, 2H). A solution of 15 mL HBr 48% was cooled to 0C. (430 mg, 2.65 mmoles) OF 3-NITROBENZONITRILE, (574 mg, 4. 85 mmoles) of Sn were added successively. The mixture was stirred at room temperature for 3 hours, then poured into ice. The solution was basified with NA2C03, extracted with CH2C12, dried, filtered and evaporated. Purified by flash chromatography on silica gel ETOH/CH2CL2 (2: 98). Yield: 32% H NMR (DMSO-d6, 300MHZ) 8 : 7.37 (M, 2H), 6.81 (M, 2H), 3.86 (s, 2H). 3-AMINOBENZONITRILE was then reacted with 2-chloroethylisocyanate as described in examples 1- 12 to obtain desired product. Purified by flash CHRMATOGRAPHY on silica gel ETOH/CH2CL2 (5: 95). Yield: 78% H NMR (CDCL3, 300 MHz) 8 : 8.12 (brs, NH, 1H), 7.26 (M, Ar, 4H), 6.97 (brs, NH, 1H), 3.63 (m, CH2,6H).

The chemical industry reduces the impact on the environment during synthesis 2-(3-Nitrophenyl)acetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; IMOTEP INC.; WO2004/106292; (2004); A1;,
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Reference of 127946-77-4,Some common heterocyclic compound, 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, molecular formula is C4H7ClN2, 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.

General procedure: To a suspension ofcompound 18 (167 mg, 1.0 mmol) in1,2-dichloroethane (8 mL), either aminoacetonitrile hydrochloride (for 30; 102 mg, 1.1 mmol) or1-aminocyclopropane-1-carbonitrile hydrochloride (for 31; 130 mg, 1.1 mmol) was added at room temperature. After 5 min,DIPEA (192 muL, 1.1 mmol) was added, followed by the slow addition of Na(OAc)3BH(276 mg, 1.3 mmol). The reaction mixture was then left to stir at roomtemperature overnight. Then, CH2Cl2 (30 mL) was added andthe mixture extracted with saturated aqueous solution of NaHCO3 (40mL). The aqueous phase was further washed with CH2Cl2 (2×50 mL), the combined organic layers were dried with anhydrous Na2SO4,filtered, and evaporated under reduced pressure. Both compounds were purifiedby flash column chromatography.

The synthetic route of 127946-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sosi?, Izidor; Mitrovi?, Ana; ?uri?, Hrvoje; Knez, Damijan; Brodnik ?ugelj, Helena; ?tefane, Bogdan; Kos, Janko; Gobec, Stanislav; Bioorganic and Medicinal Chemistry Letters; vol. 28; 7; (2018); p. 1239 – 1247;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1558-82-3, name is Ethyl N-cyanoacetimidate, A new synthetic method of this compound is introduced below., Product Details of 1558-82-3

EXAMPLE 2 Preparation of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-[(N-cyano-acetimidoyl)amino]-2H-benzo[b]pyran-3-ol To 1.23 g of ethyl N-cyanoacetimidate, 2.18 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-amino-2H-benzo[b]pyran-3-ol was added, and the mixture was stirred at a temperature of from 100 to 120 C. for 2 hours. The reaction mixture was cooled, then dissolved in 100 ml of ethyl acetate, washed twice with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The residual oily substance was recrystallized from ethyl acetate/n-hexane to obtain 1.75 g of the above identified compound in the form of crystals. Melting point: 240-243 C.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; US5095016; (1992); A;,
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Reference of 1735-53-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1735-53-1, name is 4-Bromo-3-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of [4-BROMO-3- (TRIFLUOROMETHYL)-BENZONITRILE] (Yonezawa [ET AG,] Synthetic Communications (1996) 26,1575-8 ; 2.47 g, 12 [MMOL),] 1-methylpiperazine (Fluka, Buchs, Switzerland, 5.33 mL, 48 [MMOL)] and 15 mL [N, N-DIMETHYLACETAMIDE] is stirred in a tightly closed vessel for 14 hours at [95C.] After cooling, the reaction mixture is evaporated to dryness under reduced pressure and the residue is treated with a half-saturated aqueous solution of sodium carbonate and extracted with ethyl acetate. The combined extracts are dried [(NA2SO4)] and the solvent is evaporated off under reduced pressure. The crude product is purified by column chromatography on silica gel, eluent methylene chloride/methanol to give [4- (4-METHYL-1-PIPERAZINYL)-3- (TRIFLUOROMETHYL)-BENZONITRILE] as a pale yellow oil. A mixture consisting of 30 mL dioxane, 15 mL water and 11.25 mL of 2M aqueous sodium hydroxide solution is added to [4- (4-METHYL-1-PIPERAZINYL)-3- (TRIFLUOROMETHYL)-BENZONITRILE] and the reaction mixture is shaken for 16 hours at [95C.] After cooling, the mixture is evaporated. The resulting residue is treated with water, the pH adjusted [TO-5-6] with 1 M hydrochloric acid and the solvent evaporated off under reduced pressure. The residue is treated with hot methanol, the insoluble salt filtered off and the filtrate evaporated yielding the crude title compound which is used for the next step without further purification. [‘H-NMR] (400 MHz, [DMSO-D6,] [8)] : 2.28 (s, 3H); 2.50-2. 58 (m, 4H); 2.94-3. 02 (m, 4H); 7.52 [(M, 1 H) ; 8.11-8. 17 (M, 2H); 13.19 (BR. , 1 H).]

The synthetic route of 4-Bromo-3-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/29038; (2004); A1;,
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