HCID 69522581, compound → HCID 178478965, compound

Participants

Reaction Steps

0.57 g of N-(trans-2-aminocyclohexyl)-N′-(2-chloro-6-trifluoromethylphenyl)urea in 20 ml of phosphorus oxychloride (POCl3) was boiled at reflux for 4–5 hours. The POCl3 was distilled off, water was added to the residue and the pH was adjusted to 7–8 using 2N NaOH. The mixture was then extracted with ethyl acetate, the organic solvent was distilled off and the residue was chromatographed on silica gel using a mixture of 20 parts of ethyl acetate, 10 parts of n-heptane and 3 parts of glacial acetic acid. After removal of the eluent by distillation, the white solid residue was dissolved in a little ethyl acetate and acidified using a saturated solution of HCl gas in diethyl ether. Removal of the solvent by distillation and treatment of the residue with diisopropyl ether gave 0.4 g of the desired product as a solid of m.p. 160–165° C.

Provenance & Evidence