Tag: M.W=100-200

78473-00-4, These common heterocyclic compound, 78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile, 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.

Intermediate 13: 3,5-Dichloro-4-isothiocyanato-benzonitrile To a solution of 4-amino-3,5-dichloro-benzonitrile (2.1 g, 11 mmol) and DMF (0.3 mL, 3.2 mmol) in 1,2-dichlorobenzene (15 mL) was added thiophosgene (2.6 g, 23 mmol). The resulting solution was heated to 160 C. and held at that temperature for 10 min then cooled to rt. The room temperature solution was purified by a plug of silica (220 g) using 10% EtOAc-hexanes (750 mL) to afford the title compound as a colorless solid (2.4 g, 95%). MS (ESI): mass calcd. for C8H2Cl2N2S, 227.9; m/z found, 229.0 [M+H]+. 1H NMR (CDCl3): delta 7.63 (s, 2H). 13C NMR (CDCl3): 6143.7, 133.5, 133.6, 131.5, 115.8, 111.0.

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 78473-00-4.

Reference:
Patent; Branstetter, Bryan James; Breitenbucher, James Guy; Lebsack, Alec D.; Xiao, Wei; US2008/4253; (2008); A1;,
Nitrile – Wikipedia,
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40497-11-8, Adding some certain compound to certain chemical reactions, such as: 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, 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 40497-11-8.

Sodium nitrite (224 mg, 3.25 mmol) was added carefully to sulphuric acid (concentrated, 1 ml), ensuring that the temperature did not rise above 30 C. After stirring at 15 C. for 1 h, acetic acid (2 ml) was added, followed by Preparation 36 (850 mg, 3.24 mmol) in acetic acid (3 ml). The reaction mixture was then heated at 50 C. for 1 h and cooled to room temperature. To a solution of Preparation 24 (500 mg, 3.29 mmol) in acetic acid (5 ml) was added ice water (5 ml), followed by the solution of the diazonium salt, added dropwise at 0 C. After complete addition, ammonium hydroxide (6 ml) was added and the reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered through Arbocel and the filtrate was concentrated in vacuo. The residue was partitioned between dichloromethane and water and the organic phase was separated, dried (Na2SO4) and concentrated in vacuo to give Preparation 70 (1.0 g). MS (ES): M/Z [MH+] 353.0; expected mass for C11H5Cl2F3N4S+H is 353.0 1H-NMR (CDCl3): 6.01-6.03 (1H), 7.75-7.78 (2H)

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 40497-11-8.

Reference:
Patent; Billen, Denis; Chubb, Nathan Anthony Logan; Gethin, David Morris; Hall, Kim Thomas; Roberts, Lee Richard; Walshe, Nigel Derek Arthur; US2005/148649; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 19472-74-3, name is 2-Bromophenylacetonitrile, 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 19472-74-3, 19472-74-3

A/ Preparation of 2-(2′-bromophenyl)-2-methylpropionitrile: A solution of 2-(2′-bromophenyl)-acetonitrile (7.5 g; 38 mmole) and iodomethane (16.2 g; 114 mmole) in THF (30 ml) was slowly added (60 minutes) to a suspension of NaH (4.0 g; 100 mmole) in THF (100 ml) which had been refluxed in an inert atmosphere. The reaction was exothermic. Refluxing was continued for 2.5 h. The reaction mixture was then stirred at room temperature for 15 h. The solvent was evaporated off under reduced pressure; the residue was taken up in 100 ml of water and extracted with 2*100 ml of tertiobutylmethylether. The organic phases were combined, washed with 3*100 ml of a saturated NaCl solution; dried over MgSO4 then filtered. The solvent was evaporated off under reduced pressure. The desired product was obtained as a colorless oil after distillation under reduced pressure (T=125-140 C.; p=0.1 mbar). Yield=79%. This substance was also made using the procedure described by W. E. Parham and L. D. Jones (see J. Org. Chem., (1976), 41, pp 1187-1191) with a yield of 90%. Physical characteristics: 1 H NMR (CDCl3) 1.90 ppm (s; 6H); 7.19 ppm (m; 1H; J=7.5 Hz); 7.35 ppm (t; 1H; J=7.5 Hz); 7.49 ppm (m; 1H; J=7.5 Hz); 7.67 ppm (d; 1H; J=7.5 Hz). 13 C NMR: (CDCl3) 27.13 ppm; 37.64 ppm; 123.08 ppm; 123.92 ppm; 127.76 ppm; 128.49 ppm; 130.15 ppm; 136.18 ppm; 138.77 ppm. MS (IE; 70 eV) 225/223 (M+; 80%); 210/208 (100%); 183/181 (75%); 102 (20%).

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

Reference:
Patent; Oxis Isle of Man, Limited; US5968920; (1999); A;,
Nitrile – Wikipedia,
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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

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

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

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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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;,
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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,
Nitriles – Chemistry LibreTexts

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