Phenylhydrazine → HCID 53785654, compound

Participants

Reaction Conditions

Reaction Steps

A mixture consisting of 21.88 g. (0.130 mole) p-(methylthio)benzoic acid and 25 ml. thionyl chloride was heated at the reflux temperature until evolution of gas ceased and a clear solution was obtained. After removing the excess thionyl chloride on a rotary evaporator and then under substantially complete vacuum, the solid residue that remained was dissolved in 35 ml. dioxane. The dioxane solution was mixed with a solution consisting of 14.06 g. (0.130 mole) phenylhydrazine in 100 ml. pyridine initially at 5° to 10°C. Inadvertently, about one-third of the acid chloride was added rapidly and the mixture was heated to 31°C. by the exothermic reaction. The reaction mixture was set aside at 25°C. with continuous stirring for three days. It was then poured into 1.5 l. water in order to precipitate the desired p-(methylthio)benzoic acid 2-phenylhydrazide. The precipitate was collected on a filter, washed with water, washed with 1N hydrochloride acid, and finally washed with water. The washed filter cake was then recrystallized from 3A alcohol to give 23.2 g. (69% yield) of p-(methylthio)benzoic acid 2-phenylhydrazide having a melting point at 165.5° to 167.5°C. Recrystallization from 250 ml. ethyl acetate gave the compound melting at 167° to 168°C. (shrinks at 162°C.) Two further recrystallizations from ethyl acetate gave the compound melting at 167° to 168.5°C. with shrinkage at 161.5°C.

Provenance & Evidence