Tag: M.W=100-200

194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 194853-86-6

A mixture of 4-fluoro-2- (trifluoromethyl) benzonitrile (0.158 g, 0.84 mmol), 3,3, 3- TRIFLUOROPROPYLAMINE. HCI (0.125 g, 0.84 mmol) and DIEA (0.326 g, 2.52 MMOL) in DMSO (1.5 mL) was heated under nitrogen in a microwave at 200C for 20 min. The mixture was partitioned between Et2O and 0. 1 N HCI. The organic phase was washed with 0. 1 N HCI (twice) and brine, dried (NA2SO4), and concentrated in vacuo. The residue was purified by silica gel chromatography (0-50% EtOAc-hexane gradient) and the product crystallized from ET2O-HEXANES to give the title compound as a white solid (0.144 g, 61% yield): 1H NMR (400 MHz, CDCI3) 8 7.60 (d, J = 8.6 Hz, 1 H), 6.87 (d, J = 2.4 Hz, 1 H), 6.71 (dd, J = 8.6, 2.4 Hz, 1 H), 4.56 (bs, NH), 3.53 (q, J = 6.5 Hz, 2H), 2.51-2. 40 (m, 2H); MS (ES) M/Z 283 (M+1).

Statistics shows that 194853-86-6 is playing an increasingly important role. we look forward to future research findings about 4-Fluoro-2-(trifluoromethyl)benzonitrile.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/795; (2005); A2;,
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15996-76-6, Adding some certain compound to certain chemical reactions, such as: 15996-76-6, name is 4-(Aminomethyl)benzonitrile hydrochloride, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 15996-76-6.

Synthesis of tert-butyl(4-cyanobenzyl)carbamate (7) (0149) 4-Cyanobenzylamine HCl (5.00 g, 29.7 mmol, 1.0 eq) was suspended in CH2Cl2 and NEt3 (10.3 mL, 74.1 mmol, 2.5 eq) were added to obtain a clear solution. Boc2O (8.86 mL, 38.6 mmol, 1.3 eq) was added and the solution was stirred overnight. The reaction mixture was diluted to a total volume of 100 mL with CH2Cl2 and washed with 1 M HCl (3¡Á15 mL) and sat. NaHCO3 (3¡Á15 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure. (0150) 1H NMR (500 MHz, CDCl3) delta 7.58-7.52 (m, 2H), 7.35-7.29 (m, 2H), 4.88 (s, 1H), 4.30 (d, J=6.3 Hz, 2H), 1.39 (s, 9H). (0151) 13C NMR (126 MHz, CDCl3) delta 156.2, 145.0, 132.8, 128.2, 119.1, 111.6, 80.5, 44.6, 28.8. (0152) HRMS (ESI): m/z calc. for C13H16N2NaO2+: 255.1104. found: 255.1110 (Delta=-2.0 ppm).

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 15996-76-6.

Reference:
Patent; Yale University; ERDMANN, Roman; SHRADER, Alanna Schepartz; TOOMRE, Derek; (34 pag.)US2016/115180; (2016); A1;,
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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. 21524-39-0, name is 2,3-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., 21524-39-0

Intermediate 52: 3-Fluoro-2-(2H-1 ,2,3-triazol-2-yl)benzoic acid.Step A: 3-Fluoro-2-(2H-1 ,2,3-triazol-2-yl)benzonitrile and 3-fluoro-2-(1 H- 1 ,2,3-triazol-1 -yl)benzonitrile. A mixture of 2,3-difluorobenzonitrile (4.0 g, 28.8 mmol), 2H-1 ,2,3-triazole (1 .9 g, 28.8 mmol) in DMF (85.0 mL) and K2C03 (7.9 g, 57.5 mmol) were heated to 125 C for 1 .5 h. After cooling to rt, water was added and the mixture extracted with EtOAc (2 X). The combined organics were washed with brine and dried (Na2S04). Purification via FCC (10-100% EtOAc in hexanes) gave two products. 3-Fluoro-2-(2H-1 ,2,3-triazol-2- yl)benzonitrile (1 .6 g, 29%), 1H NMR (CDCI3): 7.99 (s, J = 6.6 Hz, 2H), 7.67 – 7.63 (m, 1 H), 7.61 – 7.53 (m, 2H), 7.26 (s, 6 H) and 3-fluoro-2-(1 H-1 ,2,3-triazol- 1 -yl)benzonitrile (2.0 g, 38%) 1H NMR (CDCI3): 7.97 (dd, J = 4.4, 2.8 Hz, 1 H), 7.95 (d, J = 1 .2 Hz, 1 H), 7.70 (tt, J = 5.7, 2.8 Hz, 1 H), 7.65 (td, J = 8.1 , 4.9 Hz, 1 H), 7.62 – 7.57 (m, 1 H).

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; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); 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. 403-54-3, name is 3-Fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., 403-54-3

a. 3-Cyano-4-nitrofluorobenzene m-Fluorobenzonitrile (96.8 g., 0.8 mole) is added in two and one-half hours to a mixture of concentrated sulfuric acid (600 ml.) and potassium nitrate (80.9 g., 0.8 mole) at 3-6 C., then allowed to warm to 25 C. The mixture is poured over cracked ice (3000 ml.), extracted with chloroform (5 * 250 ml.), dried and the solvent removed. The residue is extracted with pentane and dried to give 3-cyano-4-nitrofluorobenzene (115 g., 86.5%) m.p. 102-104 C.

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Reference:
Patent; Rohm and Haas Company; US4063929; (1977); A;; ; Patent; Rohm and Haas Company; US4093446; (1978); A;; ; Patent; Rohm and Haas Company; US4046798; (1977); A;,
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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. 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., 4640-67-9

To a mixtureof 4-fluorobenzoylacetonitrile (100 g), methane sulfonic acid(230.6 g) and water (14 mL) was heated to 65-70 C, stirredfor 3 h and added a cyclooctanone (85 g) at same temperaturethen heated to 110 to 115 C stirred for 2 h, cool to room temperaturethen diluted with dichloromethane and water, organiclayer was separated and washed organic layer with water, thendistilled under vacuum solid obtained and purified with acetoneto get pure compound. Yield: 120 g; 73 %.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Sudarshan Rao; Nageswara Rao; Uma Sankara Sastry; Muralikrishna; Jayashree; Asian Journal of Chemistry; vol. 26; 18; (2014); p. 5928 – 5930;,
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21524-39-0, 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 21524-39-0 as follows.

3-Fluoro-2-(l,l-dioxo-llambda6-[l,2]thiazinan-2-yl)benzonitriQ. To a solution of l,l-dioxo-llambda6-[l,2]thiazin-2-ane (1.90 g, 14.4 mmol) dissolved in tetrahydrofuran (8 mL) and dimethylformamide (2 mL) was added sodium hydride (0.36 g, 95%, 14.4 mmol) and the mixture stirred for 20 min. To this was added 2,3-difluorobenzonitrile (2.0 g, 14.4 mmol) and the mixture stirred at 90 0C for 2 h. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and brine then concentrated. The solid residue was triturated with 1 : 1 ethyl acetate/hexane to give the title compound as a pale brown solid (0.47 g, 13% yield). 1H-NMR (500 MHz, CDCl3) delta ppm: 7.47-7.45 (IH, m), 7.32-7.36 (2H, m), 4.08-4.02 (IH, m), 3.57 (IH, td, J- 13.0, 3,7 Hz), 3.40-3.34 (IH, m), 3.32-3.27 (IH, m), 2.44- 2.32 (2HF, m), 2.04-1.97 (2H, m), 1.90-1.84 (IH, m). LCMS [M+H]+ calcd for C11H12N2FO2S: 255.28; found: 255.13.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 21524-39-0, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
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35704-19-9, Adding a certain compound to certain chemical reactions, such as: 35704-19-9, name is N-(4-Cyanophenyl)acetamide, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 35704-19-9.

PREPARATION 9 An aqueous solution (200 ml) of calcium hypochlorite (21 g) was added to a solution of p-cyanoacetanilide (12.5 g) in ethanol (27 ml), acetic acid (27 ml), and water (27 ml). The mixture was stirred for 4 days and extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated to give a powder of 2′-chloro-4′-cyanoacetanilide (12.5 g).

According to the analysis of related databases, 35704-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4866091; (1989); A;,
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95-11-4, Adding a certain compound to certain chemical reactions, such as: 95-11-4, name is 5-Norbornene-2-carbonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 95-11-4.

Example 1; Into a 50-ml glass round bottom flask equipped with a stirrer, a thermometer, a nitrogen inlet tube and a condenser were introduced 1.07 g (4.5 mmol) of nickel chloride hexahydrate, 0.60 g (9.2 mmol) of zinc, 8.90 g (28.7 mmol) of TPP containing 0.2 weight % of triphenyl phosphate purified by a known method and 26. 5 g (22.2 mmol) of CNN, and the replacement with nitrogen was surely carried out for the gas phase to obtain a tetrakis(triphenyl phosphite) nickel catalyst. Next, into a 1-L glass flat bottom separable flask equipped with a stirrer, a thermometer, a nitrogen inlet tube, a hydrogen cyanide inlet tube and a condenser were introduced 307.0 g (2.58 mol) of CNN, 90.0 g of toluene and the catalyst synthesis solution obtained as above, and the replacement with nitrogen was fully carried out for the gas phase at room temperature and then the temperature was elevated to 60 degrees centigrade. Then, 69.13 g (2.66 mol) of liquid hydrogen cyanide was supplied over 3.5 hours and hydrogen cyanide reaction was carried out to obtain 480.7 g of a coarse DCN. Nitrogen gas was bubbled in 480.7 g of the resulting coarse DCN at a flow rate of 500 ml/min for 1 hour for degassing, and then insoluble substances were filtered off. To this filtrate was added 1.9 g of 40% sulfuric acid, and the resulting solution was heated at 60 degrees centigrade for 3 hours for carrying out acid decomposition of the catalyst. 5.5 g of 25 weight % sodium hydroxide was further added thereto and the mixture was heated at 40 degrees centigrade for 2 hours and neutralized, and then 449.0 g of toluene was added for extracting DCN to obtain a DCN toluene solution. Then, toluene was removed to obtain 447.6 g of 85 weight % DCN. The resulting DCN was analyzed and as a result, triphenyl phosphate was not contained therein. Next, into a 500-ml autoclave were introduced 287.8 g of DCN obtained above, 32.6 g of 25% ammonia water and 7.9 g of a Raney cobalt catalyst, and the catalytic hydrogenation reaction was carried out at 120 degrees centigrade at hydrogen pressure of 3.5 MPa for 430 minutes. The resulting solution was cooled to room temperature and filtered to remove the Raney cobalt catalyst, and then 0.5 g of 32 weight % caustic soda was added to the filtrate for removing ammonia and toluene contained in DCN at 75 degrees centigrade at 2.6 KPa. Subsequently, the resulting residue was distilled under conditions of 0.1 MPa and a temperature in the flask of 150 to 160 degrees centigrade to obtain 204 g of NBDA. Phenol was analyzed and as a result, NBDA did not contain phenol. Furthermore, the obtained NBDA was sealed with nitrogen and then tightly closed up. The resultant was stored in a light-shielded vessel at room temperature (25 to 35 degrees centigrade) for 1 month and then time-dependent coloring was confirmed and as a result, no time-dependent coloring was found as APHA was not more than 10. The test results are shown in Table 1.; Example 2; The test was conducted in the same manner as in Example 1 using TPP containing 0.6 weight % of triphenyl phosphate. Said TPP was purified by a known method. The resulting DCN was analyzed and as a result, 0.08 weight % of triphenyl phosphate was contained therein. NBDA obtained by using this DCN contained 0.04 weight % of phenol. However, it was stored in a light-shielded vessel at room temperature (25 to 35 degrees centigrade) for 1 month and then time-dependent coloring was confirmed and as a result, no time-dependent coloring was found as APHA was not more than 10. The test results are shown in Table 1.; Comparative Example 1; The test was conducted in the same manner as in Example 1 using TPP containing 1.1 weight % of triphenyl phosphate. The resulting DCN was analyzed and as a result, 0.25 weight % of triphenyl phosphate was contained therein. NBDA obtained by using this DCN contained 0.20 weight % of phenol. It was stored in a light-shielded vessel at room temperature (25 to 35 degrees centigrade) for 1 month and then time-dependent coloring was confirmed and as a result, time-dependent coloring was confirmed as APHA was 30. The test results are shown in Table 1.

According to the analysis of related databases, 95-11-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsui Chemicals, Inc.; EP2036883; (2009); A1;,
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13388-75-5, Adding some certain compound to certain chemical reactions, such as: 13388-75-5, name is 2-(3,5-Dimethoxyphenyl)acetonitrile, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 13388-75-5.

Under a nitrogen atmosphere, add 0.2 mmol of 3,5-dimethoxyphenylacetonitrile to a 25 mL reaction flask equipped with a reflux condenser.0.6 mmol of lithium tert-butoxide, 0.6 mmol of alpha-trifluoromethylstyrene, 4 ml of dimethyl sulfoxide, the reaction system was stirred at 80C for 12 hours,Stop heating and stirring, cool to room temperature, add water to quench the reaction, add ethyl acetate to extract the reaction solution,The ethyl acetate layer was subjected to rotary evaporation under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product,The column chromatography eluent used was a petroleum ether: ethyl acetate mixed solvent with a volume ratio of 30:1; the yield of the product was 83%.

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 13388-75-5.

Reference:
Patent; South China University of Technology; Zhu Chuanle; Cai Yingying; Zeng Hao; Jiang Huanfeng; (21 pag.)CN111205202; (2020); A;,
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6136-68-1, 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. 6136-68-1 name is 3-Acetylbenzonitrile, 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.

A solution of n-BuLi (20.0 mL, 2.5 M, 50.0 mmol) was added to a solution of PPh3MeI (20.2 g, 50.0 mmol) in THF (200 mL) at -10 C. After the mixture was stirred at -10 C for 1 h, 3-acetylbenzonitrile (4.85 g, 33.4 mmol) was added. The mixture was allowed to warm up to r.t. and stirred at r.t. for 3 h. Water (400 mL) was added to the reaction mixture and it was extracted with CH2Cl2 (200 mL x 2). It was dried over anhydrous sodium sulfate, and purified by column chromatography (PE: EtOAc = 50: 1) to give the titled compound (3.4 g, 79%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Acetylbenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BURCH, Jason; GOLDSMITH, Richard, A.; ORTWINE, Daniel, Fred; PASTOR, Richard; PEI, Zhonghua; WO2013/24011; (2013); A1;,
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