2-CHLORO-2-[2-(4-CHLOROPHENYL)HYDRAZONO]-N-PHENYLACETAMIDE synthesis

Yield:33101-97-2 79%

Reaction Conditions:

with hydrogenchloride;sodium acetate;sodium nitrite in ethanol;water at 0; for 0.833333 h;

Steps:

2.2.1 2-Oxo-N-arylpropanehydrazonoyl chloride (CPD 1-2)

General procedure: Sodium acetate trihydrate (13.4g, 100mmol) was added to a stirred solution of 3-chloro-2,4-pentanedione (13.4g, 100mmol) in ethanol (200mL). After stirring for 15min, the mixture was cooled to 0°C and treated with a cold solution of aryl diazonium chloride, prepared by diazotizing aryl amines (100mmol) dissolved in 6M hydrochloric acid (60mL) with a solution of sodium nitrite (7.0g, 100mmol) in water (100mL). The addition of the diazonium salt was carried out with rapid stirring over a period of 20min. The reaction mixture was stirred for another 15min, and left 3h in a refrigerator. The resulting solid was collected and washed thoroughly with water. The crude product was crystallized from ethanol to give the corresponding hydrazonoyl chloride.

References:

El Gendy, Mohamed A.M.;Hassanein, Hamdy;Saleh, Fatma M.;Karimi-Busheri, Feridoun;Fanta, Mesfin;Yang, Xiaoyan;Tawfik, Doaa;Morsy, Shorouk;Fahmy, Merna;Hemid, Mahmoud;Abdel Azeiz, Mohamed;Fared, Ahmed;Weinfeld, Michael [Life Sciences,2022,vol. 295,art. no. 120380]