Chlorosuccinimide → N-Hydroxy-2-(trifluoromethoxy)benzimidoyl chloride

Reaction equation

C1C(=O)N([Cl:8])C(=O)C1.[F:9][C:10]([F:22])([F:21])[O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1/[CH:14]=[N:15]/[OH:16]>CN(C)C=O.O>[F:9][C:10]([F:21])([F:22])[O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1/[C:14](=[N:15]/[OH:16])/[Cl:8]

Participants

Procedure

NCS (22 g, 166.04 mmol, 1.12 equiv) was slowly added to a stirred solution of (E)-2-(trifluoromethoxy)benzaldehyde oxime (30 g, 146.27 mmol, 1.00 equiv) in N,N-dimethylformamide (300 mL) keeping the internal temperature below 25°C. The reaction mixture was stirred fo(1 h at room temperature. The resulting solution was diluted with water (300 mL) and extracted with ethyl acetate (2×500 mL). The organic layers were combined, washed with brine (5×300 mL), dried over anhydrous sodium sulfate, and concentrated under vacuum to give (Z)-2-(trifluoromethoxy)benzoyl chloride oxime as a light yellow crystalline solid.