Month: October 2020

A common compound: 139152-08-2, name is 4,5-Dichlorophthalonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 139152-08-2

Amixture of 1.0 g (5.1 mmol) of 4,5-dichlorophthalonitrile,1.9 g (10.2 mmol) of 3-phenoxyphenol 2, 4.0 g(29 mmol) of K2CO3, and 30 mL of DMF was stirredfor 5 h at 110, cooled, diluted with 200 mL of water,the separated precipitate was filtered off, washed with40 mL of 2% solution of KOH, then with water till 7,and dried. Yield 2.2 g (88%), wax-like light brownsubstance, soluble in benzene, chloroform, acetone,DMF. 1 NMR spectrum, delta, ppm: 7.43-7.34 m (8),7.27 s (2), 7.21-7.04 m (10), 6.95-6.93 m (2),6.81-6.79 m (2), 6.74 s (2), 6.59-6.53 m (4). Massspectrum, m/z: 496.26 [M]+, 543.38 [M + + 2Na]+,574.45 [M + 2K]+. Found, %: C 77.57; H 4.10; N 5.36.C32H20N2O4. Calculated, %: C 77.41; H 4.06; N 5.64.M 496.14.

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, 139152-08-2, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Koptyaev; Ageeva; Galanin; Shaposhnikov; Russian Journal of Organic Chemistry; vol. 52; 2; (2016); p. 261 – 267; Zh. Org. Khim.; vol. 52; 2; (2016); p. 278 – 283,5;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

691877-03-9, A common heterocyclic compound, 691877-03-9, name is 3-Bromo-5-(trifluoromethyl)benzonitrile, molecular formula is C8H3BrF3N, 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.

In a 20-mL glass tube equipped with a screw cap, were placed o-CP-2Cz (0.39 g), NaOtBu (0.39 g), and Pd-XPhos-OMs (0.097 g). The tube was then capped and evacuate/refill with argon three times. 0.53 mL of 1-Br-3-CN-5-CF3-C6H3 and 4.0 mL of anhydrous 1,4- dioxane were filled in under argon. The mixture was stirred at 110 C for 16 h. For work- up, the mixture was diluted with DCM and filtered through silica gel. After removing the volatiles, flash chromatography (gradient 0 to 20% DCM in hexanes) was used to purify the product. Yield: 0.41 g, 51%.

The synthetic route of 691877-03-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; BUCHWALD, Stephen, L.; HUANG, Wenliang; (89 pag.)WO2016/196885; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 935-02-4, name is 3-Phenylpropiolonitrile, 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. 935-02-4

General procedure: A solution of benzimidazole 1a-c (1.0 mmol) in dry acetonitrile (0.3 ml) was added to a solution of phenylcyanoacetylene (2) (127 mg, 1.0 mmol) and isothiocyanate 3a-c (1.0 mmol) in dry acetonitrile (0.2 ml). The reaction mixture was stirred at 50-55C for 12-20 h. The solvent was removed, and carbothioamides 4a-e were separated by chromatography on an alumina column using 20:4:1 chloroform-benzene-ethanol as the eluent.

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 935-02-4.

Reference:
Article; Andriyankova; Nikitina; Belyaeva; Mal’Kina; Afonin; Vashchenko; Smirnov; Trofimov; Chemistry of Heterocyclic Compounds; vol. 50; 6; (2014); p. 807 – 813; Khim. Geterotsikl. Soedin.; vol. 50; 6; (2014); p. 876 – 882,7;,
Nitrile – Wikipedia,
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6330-25-2, Adding some certain compound to certain chemical reactions, such as: 6330-25-2, name is 2-Cyano-N-methyl-acetamide, 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 6330-25-2.

General procedure: A mixture of beta-keto amide (0.2 mmol), ynal (0.2 mmol) and K2CO3 (30 mol%) in THF (1.0 mL) was placed in a test tube (10 mL) equipped with a magnetic stirring bar. The mixture was stirred at 65 C for 10 h. After the reaction was finished, water (5 mL) was added and the solution was extracted with ethyl acetate (3¡Á5 mL), the combined extract was dried with anhydrous MgSO4. Solvent was removed, and the residue was separated by column chromatography to give the pure sample.

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 6330-25-2.

Reference:
Article; Chen, Zhengwang; Liu, Jiayang; Jin, Caiju; Tan, Qi; Ye, Min; Tetrahedron Letters; vol. 60; 18; (2019); p. 1265 – 1267;,
Nitrile – Wikipedia,
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139152-08-2, name is 4,5-Dichlorophthalonitrile, 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. 139152-08-2

4,5-Dichlorophthalonitrile 1 (1.00 g, 5.08 mmol) and 7-hydroxy-4-(4-methoxyphenyl)-8-methylcoumarin 2 (5.73 g, 20.32 mmol) were dissolved in anhydrous dimethylformamide (DMF) (30 mL) under N2 atmosphere. After stirring for 10 min, finely ground anhydrous K2CO3 (3.50 g, 25.37 mmol) was added by stirring. The reaction mixture was stirred at 50 C for 10 days under N2 atmosphere. Then the mixture was poured in 250 ml cold aqueous solution of 5% HCl. The formed precipitate was filtered off and washed with water. After drying in vacuum at 50 C, the crude product was purified by column chromatography with silica gel eluting with DCM. Firstly, compound 3 and then compound 4 were obtained purely by using DCM and chloroform as eluting solvents, respectively.

Statistics shows that 139152-08-2 is playing an increasingly important role. we look forward to future research findings about 4,5-Dichlorophthalonitrile.

Reference:
Article; Altun, Selcuk; Oezkaya, Ali Riza; Bulut, Mustafa; Polyhedron; vol. 48; 1; (2012); p. 31 – 42;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

4640-66-8, name is 4-Chlorophenacylcyanide, 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. 4640-66-8

General procedure: 4-Chloro-3-formyl coumarin 2 (1 mmol, 208 mg), sodium azide 3 (1.25 mmol, 80 mg) and cyanoacetamide 4a (1.5 mmol, 126 mg) were taken in a round bottom flask. To this were added DMF (5 ml) and one drop of triethylamine. The reaction mixture was stirred with a magnetic stirrer at 50-60 C for 3 h. After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature and then poured into water (10 mL) with stirring. A brown coloured solid product appears. The mixture was kept in a refrigerator for 3 h. The solid product was filtered and purified by column chromatography using petroleum ether and ethyl acetate (7:3) as eluent. The structure of the compound was ascertained as 5a from the spectroscopic data and elemental analysis. Yield = 0.203 g (72.24%).

Statistics shows that 4640-66-8 is playing an increasingly important role. we look forward to future research findings about 4-Chlorophenacylcyanide.

Reference:
Article; Borah, Pallabi; Seetham Naidu, P.; Bhuyan, Pulak J.; Tetrahedron Letters; vol. 53; 37; (2012); p. 5034 – 5037,4;,
Nitrile – Wikipedia,
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1953-99-7, 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. 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3,4,5,6-Tetrachlorophthalonitrile (10 g), Potassium carbonate (10 g), Dodecane thiol (10 g) and Tetrahydrofuran (100 ml) were added to a 500 ml flask and reacted at room temperature for 2 hours.After completion of the reaction, the reaction mixture was filtered and vacuum distilled, and then hexane (100 mL) was added thereto for purification and filtration to obtain 4-dodecathio-3,5,6-trichlorophthalonitrile (11 g).

The synthetic route of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SD I Co., Ltd.; Park, In Kul; Kim, Hyung Mook; Park, Chae Won; Sin, Myung Yeop; Lee, Young Gi; Jung, Uii Soo; (31 pag.)KR2016/47824; (2016); A;,
Nitrile – Wikipedia,
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939-80-0, 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. 939-80-0 name is 4-Chloro-3-nitrobenzonitrile, 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.

Example 158(1)3-Amino-4-{4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile (158a)Compound (153a) (5.00 g), cesium carbonate (6.72 g), and 4-chloro-3-nitrobenzonitrile (3.21 g) were suspended in acetonitrile (50 mL), followed by stirring at 70 C. for 4 hr. A saturated aqueous ammonium chloride solution was added to the reaction solution, and the precipitate was collected by filtration and dried under reduced pressure to obtain 4-{4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-nitrobenzonitrile (7.19 g, 98%). The obtained 4-{4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-nitrobenzonitrile (7.19 g) was suspended in THF (50 mL), MeOH (50 mL), and water (50 mL), and ammonium chloride (7.20 g) and iron powder (8.76 g) were added to the resulting suspension, followed by stirring at 80 C. for 2 hr. The reaction solution was diluted with ethyl acetate, and insoluble matters were filtered by celite. The solvent of the filtrate was distilled away, and water was added to the residue. Insoluble matters were collected by filtration and dried under reduced pressure to obtain compound (158a) (6.44 g, 96%).1H-NMR (DMSO-d6) delta: 8.26 (1H, d, J=4.63 Hz), 8.08 (1H, d, J=4.63 Hz), 7.42 (1H, d, J=8.05 Hz), 7.23 (1H, s), 7.04 (1H, d, J=8.05 Hz), 5.80 (2H, s); LRMS (ESI) m/z 430 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-3-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; US2012/108589; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 4110-35-4 name is 3,5-Dinitrobenzonitrile, 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. 4110-35-4

(1) Ethyl 3,5-dinitrobenzimidate hydrochloride was synthesised in the same manner as in Reference Example 2. That is, 3,5-dinitrobenzonitrile (25.2 g, 0.130 mol) was treated with hydrogen chloride in ethanol (250 mL) to give 34.5 g (96%) of the target compound as pale-brown crystals.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dinitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; The Green Cross Corporation; US5948785; (1999); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

19179-31-8, Adding a certain compound to certain chemical reactions, such as: 19179-31-8, name is 3,5-Dimethoxybenzonitrile, 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 19179-31-8.

Compound 5:1-(3,5-Dimethoxy-phenyl)-pentan-1-one To Mg turnings (1.12 g, 46.7 mmol), dried in an oven for 1 hour, and dry THF (32 ml) was added 1-butylbromide (4.46 g, 32.5 mmol) and allowed to react at reflux for half an hour. After formation of the Grignard, 3,5-dimethoxybenzonitrile (4 g, 24.5 mmol) was added and the mixture was refluxed for 4 h. The reaction was cooled with ice for 15 minutes followed by the slow addition of 40 ml of 6N HCl and then the mixture was refluxed for 16 h. The THF was removed and the residue dissolved in EtOAc (60 ml) and 6N HCl (15 ml). The layers were separated, the aqueous layer extracted with EtOAc (4*20 ml). The combined EtOAc extracts were extracted and washed with saturated NaHCO3, water and brine. After drying the organic phase was concentrated and the residue resolved on silica gel eluding with EtOAc/hexanes (5:25), to yield 3.52 g (64.7%) of compound 5 as a white solid. Rf=0.43 (Hexane:ethyl acetate 9:1); IR (KBr pellet) 2956, 1601, 1206, 1067, 755 cm-1; 1H NMR delta 7.09 (d, J=2.31 Hz, 2H), 6.64 (t, J=2.31 Hz, 1H), 3.84 (s, 6H), 2.92 (t, J=7.4 Hz, 2H), 1.71 (q, J=7.71 Hz, 2H), 1.40 (s, J=7.71 Hz, 2H), 0.95 (t, J=7.32 Hz, 3H); 13C NMR delta 200.51, 161.10, 139.33, 106.17, 105.29, 55.83, 38.70, 26.84, 22.71, 14.17; MS: (ESI, Pos.) m/z 245 ([M+23]+).

According to the analysis of related databases, 19179-31-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Moore II, Bob M.; Ferreira, Antonio M.; Krishnamurthy, Mathangi; US2004/242593; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts