Category: 78473-00-4

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,
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. 78473-00-4 name is 4-Amino-3,5-dichlorobenzonitrile, 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. 78473-00-4

Step 1 : Synthesis of 4-amino-3,5-diisobutylbenzonitrile Into a 1000 mL three-neck flask were put 9.4 g (50 mmol) of 4-amino-3,5-dichlorobenzonitrile, 26 g (253 mmol) of isobutylboronic acid, 54 g (253 mmol) of tripotassium phosphate, 2.0 g (4.8 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), and 500 mL of toluene. The atmosphere in the flask was replaced with nitrogen, and this mixture was degassed while being stirred under reduced pressure. After the degassing, 0.88 g (0.96 mmol) of tris(dibenzylideneacetone)palladium(0) was added, and the mixture was stirred under a nitrogen stream at 130 C for 8 hours to be reacted. Toluene was added to the reacted solution, and the solution was filtered through a filter aid in which Celite, aluminum oxide, and Celite were stacked in this order. The obtained filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica column chromatography. Toluene was used as a developing solvent. The resulting fraction was concentrated to give 10 g of a yellow oily substance in a yield of 87 %. The obtained yellow oily substance was identified as 4-amino-3,5-diisobutylbenzonitrile by nuclear magnetic resonance (NMR) spectroscopy. The synthesis scheme of Step 1 is shown in (a-1) below.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3,5-dichlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; SEO, Satoshi; WATABE, Takeyoshi; INOUE, Hideko; YAMADA, Yui; MITSUMORI, Satomi; TAKAHASHI, Tatsuyoshi; HARA, Tomoka; (444 pag.)WO2016/203350; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile, 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. 78473-00-4

Method 2: Example 19: 3^-Dichloro-4-[4-(2,6-dimethylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitri Step 1 : 4-{[l-(4-Azidopyridin-3-yl)meth-(E)-ylidene]amino}-3,5-dichlorobenzonitrile Triethylamine (8.9 mL, 64.2 mmol) was added to a cooled (0 C) mixture of 4-azidopyridine-3-carbaldehyde (3.2 g, 21.4 mmol) and 4-amino-3,5-dichlorobenzonitrile (4.0 g, 21.4 mmol) in DCM (80 mL) under nitrogen. Titanium tetrachloride (1M, 12.8 mL, 12.8 mmol) was added and then the reaction mixture was stirred for 1 hour at 0 C. After warming to room temperature, the reaction was stirred for an additional 2 h and then concentrated under reduced pressure. The residue was suspended in toluene and filtered though a pad of Celite. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as an orange solid. This crude material was employed in the next step without further purification or analysis.

Statistics shows that 78473-00-4 is playing an increasingly important role. we look forward to future research findings about 4-Amino-3,5-dichlorobenzonitrile.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; GOODACRE, Simon; LAI, Yingjie; LIANG, Yun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/66061; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts