3,4-Dichloroaniline → 3,4-Dichloroanilinoacetonitrile

Participants

Reaction Steps

Chloroacetonitrile (45.3 grams (g)) and 97.2 g of 3,4-dichloroaniline were heated with stirring in a 250 milliliter (ml) round-bottomed three-necked flask at about 120°-125° C. for 2 hours. The reaction mixture was cooled, then diluted with methylene chloride and then filtered to remove the 3,4-dichloroaniline hydrochloride (52.4 g) which had formed. The filtrate was concentrated to dryness under vacuum, leaving a black gummy residue that crystallized on cooling. The residue was put in solution in hot toluene, the solution was then cooled and filtered, which gave 38.3 g of crude product. Recrystallization from cyclohexane gave 36.2 g of purified 3,4-dichloroanilinoacetonitrile as pink crystals, having a melting point (m.p.) of 95°-97° C.

Provenance & Evidence