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74903-80-3

4-CHLORO-N-HYDROXYBENZIMIDOYL CHLORIDE synthesis

3synthesis methods
-

Yield:74903-80-3 68%

Reaction Conditions:

with N-chloro-succinimide in N,N-dimethyl-formamide at 20; for 3 h;

Steps:

383.2 Ste 2: (0787) Preparation of (Z)-4-chloro-N-hydroxybenzimidoyl chloride

Ste 2: (0787) Preparation of (Z)-4-chloro-N-hydroxybenzimidoyl chloride: (0788) [00305] To a solution of (E)-4-chlorobenzaldehyde oxime (21.3 g, 137.08 mmol) in N, N-dimethylformamide (100 mL) was added N-chlorosuccinimide (23.70 g, 178.20 mmol) at room temperature and the reaction mixture was stirred at room temperature for 3 h. After completion of reaction, the solvent was removed under reduced pressure. The residue was diluted with cold water and stirred for 30 min. The precipitated solid filtered, washed with water and dried under vacuum to obtain title compound (Z)-4-chloro-N-hydroxybenzimidoyl chloride (17.8 g, 68% yield) as off white solid.1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.94 (s, 1H), 7.79 (d, J = 8.8 Hz, 2H), 7.53 (d, J = 8.8 Hz, 2H).

References:

WO2017/100591,2017,A1 Location in patent:Paragraph 00305