Dichloromethane → 2-((3-bromo-4-nitro-1H-indazol-1-yl)methyl)-5-methyl-1,3,4-thiadiazole

Participants

Reaction Steps

A suspension of N-acetyl-2-(3-bromo-4-nitro-1H-indazol-1-yl)acetohydrazide (0.4 g) in anhydrous THF (5 mL) was treated at ambient temperature with phosphorus(V) sulfide (0.77 g). The mixture was heated at reflux under a nitrogen atmosphere for 2.5 hours. The reaction mixture was diluted with a large excess of saturated aqueous sodium carbonate solution (50 mL) and DCM (50 mL). The resulting mixture was stirred at ambient temperature for 20 minutes, the phases were separated, and the organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude material was purified by preparative thin-layer chromatography (silica, 7% MeOH-DCM as eluent) to afford the product (235 mg) as a pale yellow solid.

Provenance & Evidence