Methyl chloroacetate → methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Participants

Reaction Steps

To 27 ml. of dimethylsulfoxide containing 5.18 g. (26.3 mmoles) of N-methylsaccharin and 4.6 ml. (52.5 mmoles) of methyl chloroacetate at 25° C. was added 14.1 g. (126 mmoles) of potassium t-butoxide in 44 ml. of the same solvent at the rate of 0.1 ml. every minute. After 42.2 ml. of the potassium t-butoxide solution had been added the addition was stopped. During the addition the reaction temperature was maintained at about 30°-32° C.

Provenance & Evidence