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

Participants

Reaction Steps

A 60% sodium hydride in mineral oil (1.1 g) was added to dry dimethylformamide (50 ml) at room temperature while stirring. Saccharin (5 g) was gradually added to the suspension at room temperature, followed by stirring for 30 minutes. To the resultant mixture, 1,4-dibromobutane (29.5 g) was dropwise added, and the mixture was kept at an inner temperature of 90° to 100° C. for 5 hours. After completion of the reaction, insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using chloroform as an eluent to give the objective compound (7.98 g). IR νmaxfilm (cm-1): 1730, 1595, 1460, 1440, 1330.

Provenance & Evidence