反应详情

A solution of ammonia (1.0 ml) in tetrahydrofuran (50 ml) at -78° was contacted dropwise with a solution of a 60/40 mixture of 2-(bromomethyl)benzenesulfonyl chloride/4-(bromomethyl)benzenesulfonyl chloride (4.52 g) in tetrahydrofuran (20 ml). The stirred mixture was allowed to warm to 0° and volatiles were removed in vacuo. The residue was contacted with water (50 ml) and extracted three times with ethyl acetate. Combined organic portions were washed with brine, dried, and evaporated to give 4.00 g of white solid. 1H nmr δ(CD3)2COTMS 8.15-7.20 (m), 6.7-6.3 (m, NH), 4.95 (q, area 21), 4.55 (s, area 18), consistent with a ca. 60/40 mixture of 2-(bromomethyl)-/4-(bromomethyl)-benzenesulfonamides. The sample was fractionally recrystallized from chloroform, but without significant change in isomeric content.

1. temperatureto warm to 0°
2. customvolatiles were removed in vacuo
3. extractionextracted three times with ethyl acetate
4. washCombined organic portions were washed with brine
5. customdried
6. customevaporated