Hydrochloric Acid → N-cyclopropyl-2-chloro-2-hydroxyimino-acetamide

Participants

Reaction Steps

To a solution of cyclopropylamine (17.5 ml, 250 mmol) in water (250 ml) was added under ice-bath cooling 4-methylene-oxetan-2-one (19.1 ml, 250 mmol) at ambient temperature upon which the pH decreased from 12 to 6.9. Stirring was continued for 10 min. Sodium nitrite (19.5 g, 275 mmol) and fuming HCl (37%; 37.5 ml, 457 mmol) were added consecutively at r.t. so that the pH always remains above pH 4.5. Into the thick foamy suspension was passed chlorine (21.3 g, 300 mmol) at r.t. over 30 min to get a light brown solution. The reaction mixture was stirred for 1 h, poured into 200 ml dichloromethane and extracted. The aqueous layers were back-extracted and the organic layers were dried and evaporated. The crude product was suspended in 10 ml diethylether, filtered and dried in vacuo to give N-cyclopropyl-2-chloro-2-hydroxyimino-acetamide (14.7 g, 36%) as light yellow solid.

Provenance & Evidence