Water → N-hydroxybenzenecarboximidoyl chloride

Participants

Reaction Steps

A solution of chlorine (1.5g) in carbon tetrachloride (42 ml) was added in portions to a stirred partial solution of benzaldehyde oxime [2.5g; 1H NMR: δ 8.18(1H,s), 9.40(1H,brs) ppm] in carbon tetrachloride (20 ml) at room temperature. Following the addition, the reaction mixture was stirred at room temperature for 3 hours then poured into water. The organic layer was separated, dried and concentrated to give almost pure α-chlorobenzaldehyde oxime (3.2g) as a yellow liquid. A solution of sodium methanethiolate (0.68g) in methanol (15 ml) was added dropwise to an ice-cooled and stirred solution of part of this α-chlorobenzaldehyde oxime (1.5g) in methanol (15 ml). Following the addition, the reaction mixture was stirred for 2 hours with continued cooling in iced-water. The methanol was removed under reduced pressure and the residue was chromatographed using dichloromethane as eluant to give a single stereoisomer of α-methylthiobenzaldehyde oxime (0.670g, 42% yield) as a white crystalline solid, m.p. 76°-78° C., 1H NMR: δ 2.08(3H,s), 9.12(1H,s) ppm.

Provenance & Evidence