4-Toluenesulfonyl chloride → HCID 54438328, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (4.6 g, 150 mmol, 80% in paraffin oil) indry THF (100 mL), a solution of 3-indazolecarboxylic acid methyl ester [(J.Am. Chem. soc, 74, 2009 (1952)] (22.0 g, 125 mmol) in dry THF (100 mL) was added dropwise with stirring while the inner temperature was maintained under 30° C. The reaction mixture was stirred for 30 minutes and then a solution of p-toluenesulphonyl chloride (28.0 g, 150 mmol) in dry THE (100 mL) was added dropwise to the stirring reactant. After 4 hours, the solvent was evaporated in vacuo and the residue partitioned between water and CH2Cl2. The organic phase was separated, dried over Na2SO4 and the solvent evaporated to leave a solid which was recrystallized from ethyl acetate (31.0 g, 75%), m.p. 163°-165° C.

Provenance & Evidence