Tag: M.W=100-200

Reference of 22364-68-7,Some common heterocyclic compound, 22364-68-7, name is 2-(o-Tolyl)acetonitrile, molecular formula is C9H9N, 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.

1-(2-Methylphenyl)acetonitrile (610 mg) was dissolved in dimethyl sulfoxide (6.1 ml), added with sodium hydride (60%, in oil, 409 mg) and stirred at room temperature for 30 minutes. This reaction mixture was added with the solution of bis(2-chloroethyl)benzylamine (1.090 g) dissolved in dimethyl sulfoxide (6.1 ml) obtained above and further stirred at 75 C. for 2.5 hours. The reaction mixture was added with water (50 ml) and extracted twice with ether (50 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=6:1) to obtain 1.077 g of the title compound. Yield: 80%. 1H-NMR (CDCl3) delta (ppm); 2.07 (2H, td, J=12 Hz, 3 Hz), 2.32 (2H, dd, J=12 Hz, 3 Hz), 2.59 (2H, t, J=12 Hz), 2.64 (3H, s), 3.01 (2H, d, J=12 Hz), 3.61 (2H, s), 7.20-7.40 (9H, m) MS (TSP); m/z 291 (MH+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(o-Tolyl)acetonitrile, its application will become more common.

Reference:
Patent; Tsushima, Masaki; Tadauchi, Kaori; Asai, Kenji; Miike, Naoko; Imai, Masako; Kudo, Toshiaki; US2003/171370; (2003); A1;,
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Synthetic Route of 147754-12-9, 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. 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-fluoro-2-methylbenzonitrile (2 g, 14.8 mmol), NBS (2.64 g, 15 mmol) and AIBN (100 mg) in CCl4 was refluxed under nitrogen for 2 hours. The reaction was cooled to room temperature. The solid was removed by filtration. The organic solution was concentrated to give crude product as an oil, which was used in the next step without further purification. 1H-NMR (400 MHz, CDCl3): delta 7.68 (dd, J= 5.2, 8.4 Hz, 1H), 7.28 (dd, J= 2.4, 8.8 Hz, 1H), 7.12 (m, 1H), 4.6 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-2-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda San Diego, Inc.; EP1586571; (2005); A1;,
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Synthetic Route of 10406-25-4, A common heterocyclic compound, 10406-25-4, name is 4-(Aminomethyl)benzonitrile, molecular formula is C8H8N2, 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 a round-bottom flask equipped with a stir bar was added 17a-b (1.0 eq), Boc2O (1.1 eq), CH2Cl2 (10mL/mmol), and triethylamine (1.5 eq). The reaction mixture was stirred at room temperature overnight. The reaction was concentrated in vacuo and partitioned between ethyl ether and 1M HCl. The organic layer were separated, washed with saturated NaHCO3 and brine, dried over MgSO4, and concentrated in vacuo to give a white crystalline solid. 4.2.4.2 128 tert-Butyl (4-cyanobenzyl)carbamate (18a) Yield: 93%. MP: 114-116C. 1H NMR (400MHz, CDCl3) delta 7.62 (d, J=7.9Hz, 2H, -ArH), 7.39 (d, J=8.5Hz, 2H, -ArH), 4.96 (s, 1H, -NH-), 4.37 (d, J=5.9Hz, 2H, -CH2-), 1.46 (s, 9H, -CH3)

The synthetic route of 10406-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Luo, Zonghua; Rosenberg, Adam J.; Liu, Hui; Han, Junbin; Tu, Zhude; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 796 – 808;,
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Electric Literature of 71825-51-9,Some common heterocyclic compound, 71825-51-9, name is 2-Methyl-2-(4-nitrophenyl)propanenitrile, molecular formula is C10H10N2O2, 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.

2-methyl-2-(4-nitrophenyl) propanenitrile (4.5 g, 23.6 mmol) was added to a reaction vessel, to which were successively added Pd/C (450 mg) and 50 mL ethyl acetate. The system was vacuumed and hydrogen was introduced. The resulting mixture is reacted at room temperature for 15 hrs. The resulting reaction was filtered with Celite, and washed with ethyl acetate. The resulting filtrate was concentrated to obtain a colorless oil of 2-(4-aminophenyl)-2-methyl propanenitrile (3.5 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methyl-2-(4-nitrophenyl)propanenitrile, its application will become more common.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; SHU, Chutian; EP2896622; (2015); A1;,
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Electric Literature of 3939-09-1, A common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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 a solution of NaH (1.2 g, 30 mmol) in toluene (50 mL) was added but-3-en-1- ol (1.8 g, 25 mmol) dropwise and the mixture was allowed to stir at room temperature for 30 minutes. 2,4-Difluorobenzonitrile (4.2 g, 30 mmol) was then added in one portion and themixture was allowed to stir at room temperature for 6 hours. Water (30 mL) was slowly added and the mixture was extracted with EtOAc and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude residue was purified using flash column chromatograpy on silica gel (20:1 PE:EtOAc) to provide compound Tnt-2b (4.2 g, 78%) as a yellow oil. ?H NMR (400 MHz, CDC13) 7.51-7.53 (m, 1H), 7.20-7.25 (m, 1H), 6.79-6.81 (m, 1H), 5.85-5.89 (m, 1H), 5.05-5.11 (m, 2H), 4.05-4.11 (m, 2H), 2.47-2.5 1 (m, 2H)

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; MERCK SHARP & DOHME CORP.; REGER, Thomas; WALJI, Abbas; SANDERS, John; WAI, John; WANG, Liping; WO2014/11769; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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 127946-77-4, Recommanded Product: 127946-77-4

Example 2; Synthesis of N-(1-cyanocyclopropyl)-2(S)-(1-benzenesulfonyliminoethylamino)-3 -(1-methyl-cyclohexyl)propionamide; (table 2, cpd 19); Step 1; To a stirred solution of 2S-fc^butoxycarbonylamino-3-(l-methylcyclohexyl)propionicacid (283 rng, 1.0 mmol) (prepared as described in Reference H except utilizing 1-methylcyclohexanol intead of 1-methylcyclopentanol) and 1-aminocyclopropanecarbonitrileHC1 salt (178 mg, 1.5 mmol) in DMF (5 mL) at room temperature was added HATU (418 mg,1.1 mmol), followed by diisopropyl ethylamine (0.87 mL, 5 mmol). After being stirred at roomtemperature overnight, the reaction mixture was concentrated under reduced pressure and thenpartitioned between ethyl acetate and brine. The combined organic extracts were dried (MgSCX),concentrated under reduced pressure, and the residue was purified by flash chromatography onsilica gel (eluted with 1: 2 EtOAc/ hexanes) to yield [l-(l-cyanocyclopropylcarbamoyl)-25′-(l-methylcyclohexyl)ethyl]-carbamic acid tert-butyl ester (315 mg, 90%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Amino-1-cyclopropanecarbonitrile hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AXYS PHARMACEUTICALS; WO2004/108661; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 403-54-3, name is 3-Fluorobenzonitrile, 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 403-54-3, SDS of cas: 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.

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

Reference:
Patent; Rohm and Haas Company; US31455; (1983); E1;,
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2042-37-7, name is 2-Bromobenzonitrile, 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. Quality Control of 2-Bromobenzonitrile

Example 2 2M Sodium carbonate solution (200 ml) was added to a stirred mixture of 4-methylphenylboronic acid (30 g), 2-bromobenzonitrile (36.4 g), palladium (II) chloride (0.4 g), methanol (200 ml) and toluene (200 ml) at 5C. The temperature rose to approximately 20C and a solid precipitated. The reaction mixture was then heated at reflux for 2 hours. The reaction mixture was allowed to cool and water (100 ml) was added, followed by diatomaceous earth (5 g). The mixture was stirred for 15 minutes, then filtered through diatomaceous earth. The organic phase of the filtrate was separated and washed with 2M sodium carbonate solution and then water. The organic phase was then filtered and the filtrate evaporated. The resultant solid was recrystallized from petroleum ether (b.p. 110-120C) to give 4–methylbiphenyl-2-carbonitrile (in 80% yield) identical to that obtained in Example 1.

The synthetic route of 2042-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENECA LIMITED; EP470795; (1992); A1;,
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Reference of 3441-01-8,Some common heterocyclic compound, 3441-01-8, name is 3-Cyanobenzamide, molecular formula is C8H6N2O, 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.

The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 4.78 g of m-cyanobenzoic acid (yield 94percent, based on m-cyanobenzamide). The m-cyanobenzoic acid obtained had a purity of 98percent.

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

Reference:
Patent; Showa Denko Kabushiki Kaisha; US6433211; (2002); B1;,
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Adding a certain compound to certain chemical reactions, such as: 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, 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 53312-81-5, Computed Properties of C7H5FN2

To a solution of 5-amino-2-fluorobenzonitrile (3.75 g) and Et3N (4.22 mL) in CH2Cl2 (100 mL) was added ethyloxalyl chloride (3.08 mL) in a dropwise fashion over 10 minutes. The reaction was stirred at RT under N2 for 1.5 h. The reaction mixture was washed with water (2×50 mL) and brine (1×50 mL), filtered through phase separatory paper and evaporated. The residue was dissolved in 20 mL of CH2Cl2 and 100 mL of hexane was added. The solution was allowed to stand at RT for the weekend. The precipitate was filtered, rinsed with hexane, and dried under vacuum to give 5.43 g of 1-(3-cyano-4-fluorophenyl)-oxoacetic acid ethyl ester. 1H NMR (CDCl3) delta1.44 (t, 3H, J=7.2 Hz, OCH2CH3), 4.44 (q, 2H, J=7.0 Hz, OCH2CH3), 7.26 (t, 1H, J=3.8 Hz, aromatic H), 7.82 (m, 1H, aromatic H), 8.04 (m, 1H, aromatic H), 8.97 (bs, 1H, NH). DCI mass spectrum z (rel. intensity) 237.1 (M+H, 6.6), 254.0 (M+Na, 100).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DuPont Pharmaceuticals Company; US6339099; (2002); B1;,
Nitrile – Wikipedia,
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