Methanesulfonyl chloride → HCID 178524175, compound

Participants

Reaction Steps

A mixture of 1,3-dichloro-2-isothiocyanato-benzene (4.50 g, 22.1 mmol) in 50 mL dichloromethane was added to a stirred solution of 3,4-diamino-benzoic acid ethyl ester (4.00 g, 22.2 mmol) in 100 mL dichloromethane. After stirring for 2 days the mixture was concentrated i.vac. The residue was taken up in 200 mL dichloromethane. TEA (7.0 mL, 49.9 mmol) and DMAP (100 mg, 0.8 mmol) were added. A mixture of methanesulfonyl chloride (1.70 mL, 22.0 mmol) in 50 mL dichloromethane was added to the solution and stirred overnight. The mixture was concentrated i.vac. The residue was taken up in methanol and 4 M NaOH (aq) was added. After stirring overnight at ambient temperature the mixture was heated to reflux for 2 h and concentrated i.vac. The residue was taken up in water and methanol and neutralized with HCl (aq). The mixture was filtered and washed with water.

Provenance & Evidence