Sulfur Dioxide → 2-aminosulfonyl-6-sec-butyl-4-methoxy-N,N-diethylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of tetramethylethylenediamine (31 mL) in THF (500 mL) at-78° C. was added sec-butyllithium (170 mL, 1.1M), followed by 2-sec-butyl-4-methoxy-N,N-diethylbenzamide (45 g) in THF (150 mL). The mixture was stirred at -78° for 15 minutes, then at 0° C. for 30 minutes, then sulfur dioxide (50 mL) was condensed into the mixture at -78° C. The mixture was warmed to -10° C., sulfuryl chloride (17 mL) was added and then the mixture was slowly warmed to room temperature and stirred overnight. The reaction mixture was added to a solution of ammonium hydroxide (94 mL) in THF (200 mL), the mixture was filtered through a pad of silica/Na2SO4 /sand to afford 51.8 g of 2-aminosulfonyl-6-sec-butyl-4-methoxy-N,N-diethylbenzamide.

Provenance & Evidence