Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 3544-25-0, name is 2-(4-Aminophenyl)acetonitrile, 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 3544-25-0, Computed Properties of C8H8N2

A solution of sodium nitrite (3.15 g, 45.7 mmol) in water (20 mL) was added dropwise to a cooled (-15 C.), stirred suspension of 4-aminobenzonitrile (5 g, 42.3 mmol) in a concentrated hydrogen chloride solution (55 mL) at such a rate as to maintain a temperature below -10 C. After the addition was finished, the reaction mixture was quickly filtered to remove solids, and the filtrate was added in portions to a cooled (-20 C.), stirred solution of SnCl2.2H2O (47.7 g, 0.21 mol) in a concentrated hydrogen chloride solution (37 mL) at such a rate as to keep the temperature below -10 C. After stirring the solution for an additional 15 minutes, the solid was collected, washed with diethyl ether (4*25 mL), and dried to give (4-hydrazinophenyl)acetonitrile hydrochloride (5.6 g, 78%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Aminophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; The Ohio State University Research Foundation; US2009/111799; (2009); 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. 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 63069-50-1

A mixture of 4-amino-3-fluorobenzonitrile (5.0 g, 36.76 mmol) and p-toluenesulfonic acid (20.0 g, 105.2 mmol) in acetonitrile (50 mL) was stirred at RT for 4 h. Then aq. solution of NaNO2 (3.8 g, 55.07 mmol) and KI (9.15 g, 55.07 mmol) were added at 0C and stirred further for lh. After the reaction completion, the reaction mixture was quenched with water, washed with an aqueous solution of NaHSO3 and extracted with EtOAc. The organic layerwas washed with water, brine, dried over Na2SO4 and concentrated to afford 4.0 g of the title product. ?H NMR (300 MHz, CDC13): 7.94-7.89 (t, J = 8.4 Hz, 1H), 7.34-7.32 (d, J = 7.5 Hz, 1H), 7.21-7.19 (d, J= 8.1 Hz, 1H).

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; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; KADAM, Sheetal R; (303 pag.)WO2016/55947; (2016); A1;,
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Some common heterocyclic compound, 14346-13-5, name is 2,5-Diaminobenzonitrile, molecular formula is C7H7N3, 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: C7H7N3

A solution of (S)-N-[1-(2-chloro-6-propylpyrimidin-4-yl)pyrrolidin-3-yl]acetamide (20 mg, 0.08 mmol) prepared in Preparation 13 and 2,5-diaminobenzonitrile (9.5 mg, 0.07 mmol) prepared in Preparation 19 in n-butanol (0.5 ml) was reacted in a microwave reactor (450 W) for 40 minutes. The reaction mixture was cooled to room temperature and then filtered to give 17.1 mg of the product as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14346-13-5, its application will become more common.

Reference:
Patent; YUHAN CORPORATION; Lee, Hyun-Joo; Kim, Dong-Hoon; Kim, Tae-Kyun; Yoon, Young-Ae; Sim, Jae-Young; Cha, Myung-Hun; Jung, Eun-Jung; Ahn, Kyoung-Kyu; Lee, Tai-Au; US2013/338179; (2013); 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. 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-(4-Fluorophenyl)-3-oxopropanenitrile

100 mL flask into a commercially available chemicals of p-fluorobenzoylacetonitrile(1) (3.2898 g, 20.16 mmol) was and suspensions put a polyphosphoric acid (20mL). This in acetone (2.4177 g, 41.63 mmol) was added and stirred for 30minutes at 80 to 90 C, and stirred for 30minutes from 140 to 150 C agitated at 30 minutes. Ice is poured into a beaker filled with a reactionliquid (100 ml), sodium carbonate powder is added carefully and neutralizedwith chloroform extracts 4 times, after drying with anhydrous sodium sulfate,distillation, solvent. Residue obtained from the recrystallization and ethylacetate, compd. 2a (2. 2037 g, 10. 84 mmol, 54%) is obtained.

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 4640-67-9.

Reference:
Patent; SHIONOGI & COMPANY LIMITED; SUZUKI, HIDEYUKI; (33 pag.)JP2016/700; (2016); A;,
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Application of 654-70-6, These common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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.

10-Chloro-2-cyclopentyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-8,10,12-trien-5-one (Intermediate 1, 157 mg, 0.56 mmol), 4-amino-2-methyl-benzonitrile (Aldrich, 95 mg, 0.51 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (27 mg, 0.05 mmol) were dissolved in 1,4-dioxane (7.5 mL). Caesium carbonate (330 mg, 1.01 mmol) was added and the mixture purged with a stream of nitrogen for 5 minutes. Tris(dibenzylideneacetone) palladium (II) (28 mg, 0.03 mmol) was added and the apparatus was evacuated and backfilled with nitrogen (×3) and then heated at 100 C. for 8 h. The mixture was cooled, filtered and the filtrate absorbed onto an SCX-3 column, washed with methanol and the product eluted with ammonia in methanol. Product containing fractions were concentrated and purified by preparative reverse phase chromatography to give the title compound as a white solid. (21 mg, 10%)1H NMR (399.9 MHz, DMSO-d6) delta1.57-1.72 (6H, m), 1.92-2.00 (2H, m), 2.61 (2H, m), 3.19 (3H, s), 3.64-3.66 (2H, m), 4.82-4.90 (1H, m), 7.99-8.07 (2H, m), 8.16 (1H, s), 8.50 (1H, d), 10.15 (1H, s); MS m/z 431 [M+H]+.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2008/9482; (2008); 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. 78881-21-7, name is 4-Amino-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

A mixture of 6-chloro-4-isopropyl-N- (tetrahydro-pyran-4-ylmethyl)-nicotinamide (Description 24) (100mg), 4-amino-3-methyl benzonitrile (2eq), cesium carbonate (168mg), tris (dibenzylideneacetone) palladium (0) (Pd2 (dba) 3) (3.4mg), 4,5-bis (diphenylphosphino)-9, 9- dimethylxanthene (Xantphos) (2.3mg) in 1, 4-dioxane (lml) was irradiated under microwave conditions at 150C for 30 minutes. Further quantities of cesium carbonate (168mg), Pd2 (dba) 3 (3.4mg) and Xantphos (2.3mg) were added and the mixture was again subjected to microwave conditions at 150C for 30 minutes. Ethyl acetate was added and the mixture was washed with water. The ethyl acetate layer was dried (sodium sulphate) and the solvent was removed under reduced pressure. The residue was purified using MDAP to give the title compound (20mg) NMR (MeOD) 8 1.25 (6H, d), 1.29-1. 43 (2H, m), 1. 70 (2H, d), 1.81-1. 93 (1H, m), 2.3393H, s), 3. 2 1- 3.50 (5H, m), 3.98 (2H, dd), 7.01 (1H, s), 7.49 (1H, dd), 7.55 (1H, bs), 8.02 (1H, d), 8.09 (1H, s) LC/MS, t = 2.89 min, Molecular ion observed [MH+] = 393 consistent with the molecular formula C23H28N402

According to the analysis of related databases, 78881-21-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; DOUGHTY, Jennifer, Margaret; WO2005/74939; (2005); A1;,
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Reference of 21803-75-8, 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. 21803-75-8, name is 4-Amino-3-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Compound 3b (390.0 g, 1.00 mol) was dissolved in 800 mL 2-Me-THF followed by the addition of triethylamine (TEA, 232.5 g, 2.30 mol). The light yellow solution was cooled to 5 C. Methanesulfonyl chloride (126.0 g, 1.10 mol) was added within 1 h while maintaining the temperature at 5 C. The reaction was continued for 1 h at 5 C. A solution of 4b (4-amino-3- chlorobenzonitrile) (167.0 g, 1.10 mol) in 300 mL 2-Me-THF was added and the slurry was heated to reflux (-84 C), followed by stirring under reflux for 4 h. The reaction mixture was cooled to 20 C and the precipitate was removed by suction filtration. The product cake was washed with 200 mL 2-Me-THF. The mother liquor was used as such in the next step.

The chemical industry reduces the impact on the environment during synthesis 4-Amino-3-chlorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; INTERVET INTERNATIONAL B.V.; BRINK, Monika; NIEDERMANN, Hans-Peter; KNELL, Marcus; FENG, Tao; TRZASKA, Scott, T.; COOPER, Arthur, J.; DESAI, Shaileshkumar Ramanlal; GORE, Vinayak Keshav; WO2012/85645; (2012); 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. 17626-40-3, name is 3,4-Diaminobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 17626-40-3

General procedure: Diisopropylcarbodiimide 82 mul (66.9 mg, 0.53 mmol, 1.20 equiv) DIC was added to a solution of 4-chlorobenzoylpyruvic acid 100 mg (0.44 mmol, 1.00 equiv) 12b and 73.8 mg (0.53 mmol, 1.20 equiv) of HOBt [CAS: 123333-53-9, 97% wetted with ? 14 wt % H2O] in 3.0 ml of DMF (abs) under Ar. The reaction mixture was stirred for 5 min. Then o-phenylenediamine (1.00 mol equiv) from 11a-f was added and the mixture was stirred at rt under Ar for 72 h. The precipitated product mixture obtained after filtration (or centrifugation) was triturated by 3 ml of Et2O and crystallized from DMSO (if not otherwise stated) to yield the main solid regioisomer 16 or 17.

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:
Article; Dobia?, Juraj; Ondru?, Marek; Addova, Gabriela; Boha?, Andrej; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 1350 – 1360;,
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Synthetic Route of 654-70-6, 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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Lithium bis (trimethylsilyl) amide (LHMDS) (5 eq.) was added to a solution of 4-cyano-3-trifluoromethyl aniline (1.6 eq.) in dry THF (1 mL x mmol aniline) at -5C. After stirring for 45 min., hexamethylphosphoric triamide (HMPA) (20% of the previously added, THF) . After 5 min at -5C a solution of (R) -XVIII-5 in THF (1.5 mL x mmol of (.R)-XVIII-S) was added drop wise. After 30 min at 00C, the reaction mixture was allowed to warm up at the temperature value (25C) and than stirred for additional 6/7 h. The reaction was than quenched with an NH4Cl saturated solution and extracted with ethyl acetate. Silica gel column chromatography or crystallization, afforded the pure compound.(R) -XXIV-I: 1H NMR (400 MHz, CDCl3) : bs, IH, NH) , 7.69 (d, J= 8.8Hz, 2H, 7.53-7.48 (m, 3H, ArH) , 7.39-7.26 (m, H) , 6.84 (t, J= 8.2Hz, 2H, ArH) , 3.90(d, J= 14.4Hz, IH, CH2) , 3.78 (bs, IH, OH) , 3.26 (d, J= 13.6Hz, IH, CH2) , 3.07 (d, J= 14.4Hz, IH, CH2) , 2.95 (d, J= 13.2Hz, IH, CH2)

The synthetic route of 4-Cyano-3-trifluoromethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; ISTITUTO SCIENTIFICO ROMAGNOLO PER LO STUDIO E LA CURA DEI TUMORI (I.R.S.T.) S.R.L.; VARCHI, Greta; TESEI, Anna; GUERRINI, Andrea; BRIGLIADORI, Giovanni; WO2010/116342; (2010); A2;,
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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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(Methylamino)acetonitrile hydrochloride

A. N-Carbophenoxy-N-methylaminoacetonitrile To a suspension of methylaminoacetonitrile hydrochloride (100 g; 0.94 mole) in 1 liter of methylene chloride (cooled in an ice-water bath) was added triethylamine (260 ml, 1.88 moles) and a solution of phenyl chloroformate (155.0 g; 0.99 mole) in 500 ml of methylene chloride. The reaction mixture was heated at reflux temperature for 18 hours, then evaporated under reduced pressure to give a semi-solid which was triturated with 1 liter of diethyl ether and filtered. The filtrate was evaporated under reduced pressure and the residual oil was vacuum distilled to yield the title compound (123 g), bp 111°-113°/0.25 mm Hg; the NMR spectrum (60 MHz) in CDCl3 gave the following resonances delta: 7.23 (m, 5H); 4.30 (s, 2H); 3.13 (s, 3H).

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 25808-30-4.

Reference:
Patent; Bristol-Myers Company; US4471122; (1984); A;; ; Patent; Bristol-Myers Company; US4510309; (1985); A;; ; Patent; Bristol-Myers Company; US4394508; (1983); A;,
Nitrile – Wikipedia,
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