Bromine → HCID 178422443, compound

Participants

Reaction Conditions

Reaction Steps

A solution of bromine (0.336 g, 2.1 mmol) in glacial acetic acid (1 ml) was added dropwise to a stirred solution of N-cyclohexyl-N'-(2-methylphenyl)guanidine (0.231 g, 1 mmol) in glacial acetic acid (2 ml) at room temperature. After the addition, the addition funnel was replaced by a reflux condenser and the red reaction solution was heated on a warm water bath at 70° C. for about an hour. The reaction mixture was allowed to cool to room temperature and then poured in cold ice water (30 ml) containing a 200 mg of sodium bisulfite. The mixture was then extracted with dichloromethane (3×15 ml) and the combined organic layers were dried over sodium sulfate, filtered and concentrated to give a colorless liquid (0.475 g). This liquid was purified on a flash silica gel column to give a bright foamy product (0.25 g), mp 89°-91° C.

Provenance & Evidence