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ChemicalBook CAS DataBase List 2-Chloro-N-(4-nitrophenyl)benzamide

2-Chloro-N-(4-nitrophenyl)benzamide synthesis

6synthesis methods
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Yield:55501-45-6 60%

Reaction Conditions:

Stage #1: ortho-chlorobenzoic acidwith dmap;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane at 20; for 0.5 h;
Stage #2: 4-nitro-aniline in dichloromethane at 20; for 16 h;

Steps:

1.1. General procedure for the preparation of the 2-methyl-N-(4-nitrophenyl)benzamide derivatives 12a-u

General procedure: Substituted benzoic acid (11a-u, 8 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI, 1.69g, 8.8 mmol), and 4-dimethylaminopyridine (DMAP, 0.1 g, 0.08 mmol) were dissolved in dichloromethane (DCM, 16 mL) and stirred for 30 min at ambient temperature. 4-Nitroaniline (1g, 7.2 mmol) was added, and the mixture was stirred at ambient temperature for 16 h. Upon completion, the reaction mixture was poured into water and extracted with DCM. The combined organic phases were dried with anhydrous Na2SO4, filtered, and concentrated in vacuo to afford compounds 12a-q.

References:

Wang, Ru;Liu, Hu;You, Yuan-Yuan;Wang, Xin-Yu;Lv, Bing-Bing;Cao, Li-Qin;Xue, Jia-Yu;Xu, Yun-Gen;Shi, Lei [Bioorganic and Medicinal Chemistry Letters,2021,vol. 36,art. no. 127788] Location in patent:supporting information