Synthesis
To a 250 mL round bottom flask was added 5.8 mL (63.76 mmol, 1.05 eq.) of a 150 mL solution of aniline in anhydrous dichloromethane, and 14.8 mL (106.26 mmol, 1.75 eq.) of triethylamine was slowly added at 0 °C and stirred for 30 min. Subsequently, 11.479 g (60.72 mmol, 1.0 eq.) of 2-chloro-6-methylbenzoyl chloride was added slowly dropwise, maintaining the reaction temperature at 0 °C and stirring the reaction for over 3 hours. Upon completion of the reaction, the mixture was washed sequentially with 1N HCl, water and aqueous sodium bicarbonate each. The organic layer was dried over anhydrous sodium sulfate and purified by recrystallization to give 13 g (52.91 mmol, 87% yield) of 2-chloro-6-methyl-N-phenylbenzamide as a white solid.
References
[1] Patent: KR2017/74381, 2017, A. Location in patent: Paragraph 0191; 0192; 0195; 0196
[2] Patent: KR2017/74380, 2017, A. Location in patent: Paragraph 0224; 0225; 0228; 0229
[3] Patent: WO2017/188720, 2017, A2. Location in patent: Paragraph 220
[4] Patent: US2018/105527, 2018, A1. Location in patent: Paragraph 0508-0510
[5] Patent: US2012/184568, 2012, A1. Location in patent: Page/Page column 79
