Carbon Disulfide → HCID 12925584, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-methyl aniline (10.71 g, 100 mmol) in DMSO (50 mL) was treated with 20N aqueous NaOH (5 mL, 100 mmol) at room temperature. The mixture was cooled to 0° C. and CS2 (7.61 g, 100 mmol) was added. Upon stirring for 1 hour at room temperature, a change of color from dark-red to orange was observed. The solution was then cooled to 0° C. and chloroacetone (9.25 g, 100 mmol) was added. After stirring for 3 hours at room temperature, water (100 mL) was added and the mixture was stirred for an additional 10 minutes at 0° C. The precipitate was filtered and successively washed with water and ethanol. The crude product was suspended in 95% ethanol (100 mL), and 36% HCl (50 mL) was added and the mixture was heated to reflux for 1 hour. After cooling to room temperature, the precipitate was filtered to yield the desired product. (8.7 g, 38%)

Provenance & Evidence