Novel 3-halo-2-hydroxyalkyl carbamates

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...

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544388, 544398, C07C12506

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active

046297910

ABSTRACT:
The invention is a compound which comprises one or more 3-halo-2-hydroxyalkyl carbamate moieties; wherein the carbamate nitrogen is tertiary. In preferred embodiments, the carbamate nitrogen is tertiary, and the carbamate nitrogen is further substituted by an alicyclic or aliphatic moiety or is part of a heterocyclic ring, wherein the heterocyclic ring can contain an oxygen or sulfur atom or may contain another tertiary 3-halo-2-hydroxyalkyl carbamate moiety; or wherein two or more of such 3-halo-2-hydroxyalkyl carbamates are linked by an aliphatic or alicyclic moiety.
Another aspect of the invention is a process for the preparation of such 3-halo-2-hydroxyalkyl carbamates which comprises contacting an epihalohydrin carbonate with a secondary amine-containing compound, wherein the secondary amine has a pKa at which the secondary amine will react with the epihalohydrin carbonate and which does not catalyze the formation of unwanted by-products, in a polar organic solvent under conditions such that a 3-halo-2-hydroxyalkyl carbamate, wherein the carbamate nitrogen is tertiary, is prepared.

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