Dimethylformamide → HCID 67641417, compound

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Reaction Steps

A mixture of 2,4-dihydro-2--phenyl-5-cyano-3H-pyrazol-3-one (Formula III: R1 =Ph; R2 =CN; R3 =H) (366 mg; 1.98 mmol), 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (689 mg, 1.98 mmol), and KF (230 mg, 3.91 mmol) in 8 ml of DMF was stirred at room temperature for 3 hours and the resulting mixture was diluted with ice/water. The solid product was filtered, the residual solid was redissolved in ether/water, and the aqueous layer was extracted with ether (3×). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo, and the residue was purified by column chromatography (silica gel; 12-50% ethyl acetate in hexane) and recrystallized from ethyl acetate/hexane to afford 420 mg (47%) of 4-isopropyl-6-methoxy-2-(1-phenyl-3-cyanopyrazol-5-yl-oxymethyl)-1,2-benziso thiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =Ph; R2 =CN; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 114°-116° C.

Provenance & Evidence