Diethyl Ether → Cyclohexylsulfamate

Participants

Reaction Steps

15.6 g (0.05 mol) of 1-[p-(2-acetylamino-2-carbomethoxyvinyl)-phenoxy]-2,3-epoxy-propane are dissolved in 50 ml of absolute tetrahydrofurane, 4.25 ml (0.05 mol) of isopropylamine are added and thereafter the mixture is heated for 18 hours to the boil under a reflux condenser. It is then evaporated in vacuo and the resulting crude base is dissolved in ethyl acetate. The solution is extracted three times with 20 ml of 1 N hydrochloric acid at a time. The hydrochloric acid extracts are brought to pH 8 with sodium carbonate solution and the crude base which hereupon has separated out is extracted with ethyl acetate. The extract is washed with water, dried over sodium sulphate and evaporated in vacuo. 17 g of crude base are obtained as a brownish oil. This is dissolved in 20 ml of acetone and mixed with a solution of 9 g of N-cyclo-hexylsulphamic acid in 70 ml of acetone. After addition of ether, the N-cyclohexylsulphamate of 1-[p-(2-acetylamino-2-carbomethoxy-vinyl)-phenoxy]-2-hydroxy-3-isoproylamino-propane, melting point 121°-125°C, is obtained.

Provenance & Evidence