Triethylamine → Hydrochloric Acid

Participants

Reaction Conditions

Reaction Steps

Ethyl chloroformate (23.88 g, 0.22 mole) was added dropwise to a solution of 6-amino-2-mercaptobenzothiazole (18.23 g, 0.1 mole), triethylamine (22.26 g, 0.22 mole), 4-dimethylaminopyridine (100 mg) in N,N-dimethylformamide (100 ml) with stirring at 0° C. over a 1/2 hour period. The mixture was brought to ambient temperature then stirred for 2 hours. The reaction mixture was added to dilute aqueous hydrochloric acid-ice to precipitate a solid product. Reprecipitation by dissolution in aqueous sodium hydroxide solution then acidification with 12N HCl gave 17.50 g of 6-(N-ethoxycarbonylamino-2-mercaptobenzothiazole, m.p. 310°-312° C.

Provenance & Evidence