Aniline → HCID 10703669, compound

Participants

Reaction Steps

65.1 g (0.3 mole) of N-cyclohexyl-m-toluamide were dissolved in 500 ml of dried tetrahydrofuran and a benzene solution of 45 g of COCl2 absorbed in 30 ml dried benzene, and 30 ml dried pyridine were added dropwise and under agitation and ice cooling to the above tetrahydrofuran solution. Upon completion of the dropwise addition, the reaction mixture was adjusted in its temperature to room temperature and brought into reaction for 2 hours. The sedimented pyridine hydrochloride were filtered off and the filtrate was condensed under vacuo, to provide an oily substance containing N-cyclohexyl-m-toluimido chloride. The oil was then subjected to extraction with 400 ml of dried petroleum ether and 32.8 ml (0.36 mole) of aniline were added dropwise for 30 minutes under agitation and ice cooling to the extract and the mixture was let to react at room temperature for 1.5 hours. The thus deposited oily substance was decanted off from the mother liquor and dissolved in 100 ml of ethanol, adjusted pH to about 2 by addition of 1N-hydrochloric acid and added with 1.2 lit. of water. Then, the aqueous solution was washed twice with 150 ml of ethyl acetate. The aqueous phase was treated with active carbon for discoloration and then condensed under vacuo. The sedimented products were filtered off, washed, dried and recrystallized from ethanol/diethyl ether. In this way, 81.7 g of N-cyclohexyl, N'-phenyl-m-toluamidine were obtained. m.p. 174° - 176° C. Yield: 82.9%.

Provenance & Evidence