Cyanide → HCID 21329847, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 19.6 g of p-chloro-α,α-dimethylbenzyl isocyanate, prepared from the corresponding cyanide in the same way as in Synthesis Example 1, in 10 ml of diethyl ether was added dropwise to a solution of 10.9 g of N-phenylhydroxylamine in 10 ml of diethyl ether. After completion of the addition, the mixture was stirred for 30 minutes whereby 3-(p-chloro-α,α-dimethylbenzyl)-1-hydroxy-1-phenylurea precipitated. The resulting crystals were separated by filtration and dried. A 3.0 g portion of the crystals thus obtained was added to 10 ml of an ethanolic solution of 750 mg of sodium ethoxide, and, after the crystals had been completely dissolved, 1.2 g of ethyl bromide was added thereto followed by heating at 60° C. for 2 hours. The solvent was then removed by distillation under reduced pressure, and the resulting residue was extracted with water and benzene. The benzene layer was washed successively with 2N aqueous sodium hydroxide and water and dried over anhydrous sodium sulfate. The solvent was removed by distillation to precipitate crystals which were then recrystallized from a mixture of benzene and hexane to obtain 3.1 g of the title compound as white crystals.

Provenance & Evidence