4-bromo-2-isocyanato-1-methylbenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 16.5 grams of 5-bromo-2-methyl aniline and 100 ml. of ethylacetate was added with stirring to a solution of 20 grams of phosgene and 300 ml. of ethylacetate kept at 5° C. After the addition was completed, phosgene was bubbled through the mixture while refluxing for one-half hour. The reaction mixture was purged with nitrogen, then the solvent was removed in vacuo to obtain 17 grams of 5-bromo-2-methylphenylisocyanate. This material was dissolved in 150 ml. of chloroform and added cautiously to a solution of 18.2 grams of 3-chloropropylamine hydrochloride, 150 ml. of chloroform, and 20 ml. of triethylamine. The mixture was refluxed for one-half hour, then cooled and shaken with water. The precipitated solid was separated by filtration. Recrystallization from ethylacetate afforded N-[3-(chloropropylamino)propyl]-N'-(5-bromo-2-methylphenyl)urea, m.p. 145°-148° C. kept at 5° C After the addition phosgene was bubbled through the mixture while refluxing for one-half hour The reaction mixture was purged with nitrogen the solvent was removed in vacuo