Optically active 1-oxyethyl-4-phenyl-2-imidazolidones

Details Optically active 1-oxyethyl-4-phenyl-2-imidazolidones Optically active 1-oxyethyl-4-phenyl-2-imidazolidones

1976-11-08

1978-05-02

Trousof, Natalie

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

2603068F, 260307F, 424270, C07D23332, C07D23338

Patent

active

040876110

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: 3726894 (1973-04-01), Spicer
Fieser et al., Advanced Organic Chemistry, pp. 73-88, N.Y. Reinhold, 1961.
Rodionou et al., Chem. Abst., 1949, vol. 43, col. 3821.
Kametani, Chem. Abst., 1952, vol. 46, col. 4547-4548.

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