Verfahren zur Herstellung neuer, halogenhaltiger Carbamidsaeureester

摘要

The invention comprises compounds of general formula: in which R1 denotes an alkyl, substituted alkyl, cycloalkyl, aryl, aralkyl, amino, substituted amino, carbamyl, substituted carbamyl or heterocyclic radical, R2 denotes a hydrogen atom or an alkyl, substituted alkyl or aryl radical, or in which R1 and R2 together with the amide nitrogen atom may form a heterocyclic ring, and in which X1, X2, X3 are each halogen atoms; and their preparation by introducing the radical -CO-NR1R2 into a pentaerythritol trihalohydrin of general formula: to replace the hydroxyl hydrogen thereof by reacting said pentaerythritol trihalohydrin with a carbamic acid halide of general formula: Hal-CO-NR1R2, or with phosgene and then with an amine of general formula HNR1R2, or (when R2=H) with an isocyanate of general formula OCN-R1. Other processes described are reaction of a pentaerythritol trihalohydrin with (1) a urethane R3O.OC-NR1R2, or (2) a haloformic acid ester Ha1-CO.OR3 and then with an amine HNR1R2, or (3) with phosgene and an alcohol R3OH to form a mixed carbonic acid ester and then with an amine HNR1R2. Chloroformic acid-(2, 2, 2-trischloromethyl)-ethyl ester is prepared by reaction of phosgene with the corresponding hydrin. Pharmacological formulations containing compounds of the invention are mentioned for oral, parenteral and rectal administration. The compounds have sedative and hypnotic properties. Specification 780,713 is referred to.