Potassium Iodide → 1-Allyl-1-phenyl-2-(3-sulfamoyl-4-chlorobenzoyl)-hydrazine

Participants

Reaction Steps

A mixture of 3-aminosulfonyl-4-chloro-benzhydrazide (326.6g, 1.0 mole) sodium bicarbonate (420.0g, 2.0 mole), potassium iodide (16.6g, 0.1 mole) and allyl bromide (242.0g, 2.0 mole) in isopropanol (1,500 ml) was stirred at gentle reflux for 20 hours, then cooled to 50° and filtered by suction. The cake was washed twice with 100 ml portions of isopropanol. The washes and filtrate were combined and diluted with sufficient water to make a 70% isopropanol solution, then allowed to stir overnight to complete crystallization. The crude product was filtered and washed twice with 100 ml portions of isopropanol-water (70:30). One recrystallization from isopropanol-water (70:30) and clarification with activated charcoal gave pure compound in 80% yield.

Provenance & Evidence