Dimethyl Sulfide → 2-Chloro-6-methylsulfanylmethyl-phenylamine

Participants

Reaction Steps

2-Chloro-phenylamine (12.76 g, 0.1 mole) and dimethyl sulfide (10 ml) were dissolved in dichloroethane (200 ml) and cooled in an ice-acetone-salt bath under a nitrogen atmosphere. N-chlorosuccinimide (14.70 g, 0.11 mole) dissolved in dichloroethane (300 ml) was slowly added via addition funnel over about 20-30 minutes. After stirring an hour beyond addition while allowing the reaction to reach room temperature, triethyl amine (30 ml) was added and the mixture was brought to reflux for 1 h and 20 minutes. The reaction was monitored by tlc (15:85 EtOAc:hexane on silica gel) which showed a single less polar product. The mixture was cooled and evaporated to dryness. The residue was taken up in methylene chloride, dry packed on silica gel, and placed onto a column of flash silica gel. The product was eluted from the column with 1:9 ethyl acetate:hexane to give 15.4 g of a homogeneous oil (82%), 2-chloro-6-methylsulfanylmethyl-phenylamine.

Provenance & Evidence