Chlorine → N-Chlorophthalimide

Participants

Reaction Conditions

Reaction Steps

Chlorine gas was bubbled into one liter of methylene chloride maintained at 0° C. The chlorine was added for about 10 minutes and until saturation was achieved. To the resulting chlorine-saturated methylene chloride were added 50 grams (270 mmoles) of potassium phthalimide as a solid and in one portion. The resulting mixture was allowed to warm gradually to 20° C., and additional chlorine was introduced as a gas during two separate periods to ensure the presence of an excess of chlorine. The mixture then was stirred vigorously at 20° C. for 60-90 minutes. The resulting precipitated potassium chloride was removed by filtration, and the filtrate was evaporated in vacuo to dryness. The residual white solid was suspended in 150 ml. of water for a few minutes, filtered, and washed with 100 ml. of water. The solid was vacuum dried overnight to obtain 44.5 grams (91% yield) of N-chlorophthalimide.

Provenance & Evidence