Dimethylformamide → 3-(3-chloropropyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl)propan-1-ol (1.0 g, 4.1 mmol) in dichloromethane (20 mL) was treated with thionyl chloride (0.91 mL, 12.3 mmol) and dimethylformamide (0.20 mL) and stirred at 23° C. for 16 hours. Additional thionyl chloride (0.30 mL, 4.1 mmol) was added and stirring was continued for an additional 4 hours. The reaction mixture was quenched by the addition of methanol (5 mL) and evaporated. Flash chromatography (SiO2, 3-40% ethyl acetate/hexanes) provided 3-(3-chloropropyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.85 g, 79%) as a yellow oil:

Provenance & Evidence