Synthesis of tetramisole, levamisole and their derivatives

Details Synthesis of tetramisole, levamisole and their derivatives Synthesis of tetramisole, levamisole and their derivatives

1978-02-15

1982-02-02

Raymond, Richard

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D23338

Patent

active

043140661

ABSTRACT:
A process for the manufacture of 1-(2-alkoxyethyl)-4-phenyl-4-imidazolin-2-ones, 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones, 1-(2-alkoxyethyl)-4-phenyl-imidazolidine-2-thiones, certain of the corresponding 1-(2-hydroxyethyl) derivatives, and their 3-acylated derivatives, and certain related compounds which are all useful as intermediates in a new process for the manufacture of the anthelmintic levamisole, (-)-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazole, and its derivatives through conventional resolution procedures. The new process also permits the direct manufacture of optically active 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidone and their 3-acylated derivatives, optically active 1-(2-alkoxyethyl)-4-phenylimidazolidine-2-thiones, and levamisole, the levorotatory isomer of tetramisole, using catalytic amounts of a chiral reducing agent, with the elimination of conventional resolution procedures.

REFERENCES:
patent: 2441935 (1948-05-01), Duschinsky
patent: 3849480 (1974-11-01), Knowles
patent: 4119652 (1978-10-01), Knowles
Hofmann, Imidazole and Its Derivatives, Part 1, Interscience Publishers, New York (1953), pp. 235-236.

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