Methyl iodide → 1-Methyl-5-nitro-1,3-dihydrobenzo[c]isothiazole 2,2-dioxide

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Reaction Conditions

Reaction Steps

NaHCO3 (0.2 g, 2.4 mmol) is dissolved in H2O (3 mL) and 5-Nitro-1,3-dihydro-2H-2,1-benzisothiazole-2,2-dione (1) (0.41 g, 1.9 mmol) is added with stirring. The mixture is heated to 80° C. for 0.5 hrs and a yellow solid formed. The mixture is cooled to 0° C. and filtered. The solid is washed with cold H2O (5 mL) then with cold EtOH (15 mL). The yellow solid thus obtained is dried under high vacuum then dissolved in dry DMF (3.5 mL). Iodomethane (0.15 mL, 2.1 mmol) is added and the solution heated to 100° C. for 2 hrs. The solution is cooled to room temperature then poured into ice water (50 mL). The solid is collected by filtration and gave crystals (0.27 g, 62%) after recrystallization from EtOH. Mp 214-6° C. HRMS (FAB) calcd for C8H8N2O4S +H1 229.0283, found 229.0280.

Provenance & Evidence