Dimethylformamide → 1,1-Dioxido-2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

The general procedure of J. D. Commerford and H. B. Donahue J. Org. Chem. 1956, 21, 583-4 was modified: A mixture of 6 g of sodium saccharin, 100 mL of 1,4-dibromobutane, and 5 mL of N,N-dimethylformamide was heated at 50° C. overnight. After cooling to ambient temperature, the mixture was diluted with 250 mL of ether and 50 mL of water. The aqueous layer was extracted with two additional 50 mL portions of ether and the combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. The excess 1,4-dibromobutane was removed by short path vacuum distillation and the oily residue purified by crystallization from ether-hexane, mp 71-2° C.

Provenance & Evidence