Sulfur Dioxide → HCID 13178728, compound

Participants

Reaction Steps

To a solution of 53.5 g of the product of Example 3 in a mixture of 225 ml of concentrated hydrochloric acid and 75 ml of glacial acetic acid was added a solution of 21.4 g of sodium nitrite in 70 ml of water at -5° to 0°. The solution was stirred at 0° for 15 minutes, then poured into a mixture of 6 g of cuprous chloride, 48 ml of liquid sulfur dioxide in 300 ml of glacial acetic acid at 0°-4°. This mixture was stirred at 0° for 1 hour, then at 25° for 2 hours before being poured into 2 liters of ice-water. The precipitate was filtered and washed with water then suspended in 250 ml of ether and treated with 11.0 ml of liquid anhydrous ammonia at 5°-15°. After stirring at 25° for 30 minutes the precipitate was filtered off and washed well with ether then water. Oven drying at 60° gave 40.2 g of 2-[(dimethylamino)sulfonylmethyl]benzenesulfonamide, m.p. 145°-150°.

Provenance & Evidence