Process for the preparation of halohydroxyalkyl carbamates and 2

Details Process for the preparation of halohydroxyalkyl carbamates and 2 Process for the preparation of halohydroxyalkyl carbamates and 2

1985-04-05

1988-05-03

Hollrah, Glennon H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

544357, 544385, 544386, 544 54, 544 584, 544 88, 544172, 546226, 546245, 548201, 548215, 548341, 549539, 560115, 560158, 560166, C07D24104

Patent

active

047421690

ABSTRACT:
The invention is a process for the preparation of halohydroxyalkyl 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 the further presence of an acid scavenger capable of forming a salt with the hydrogen halide by-product formed, in an amount sufficient to prevent the formation of unwanted by-products, in a polar organic solvent under conditions such that a halohydroxyalkyl carbamate, wherein the carbamate nitrogen is tertiary, is prepared.
Another aspect of this invention is the further step of contacting the 3-halo-2-hydroxyalkyl carbamate with an ion-exchange resin with pendant moieties containing hydroxide moieties in a lower alkanol solvent under conditions such that the 3-halo-2-hydroxyalkyl moieties are converted to 2,3-epoxyalkyl moieties so as to prepare a 2,3-epoxyalkyl carbamate.

REFERENCES:
patent: 3872097 (1975-03-01), Habermeier et al.
patent: 4501874 (1985-02-01), Hanafin

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