American Cyanamid Company

Cyanamid Agricultural De Puerto Rico, Inc.

Sivaraman Raghu

Arthur K Hoffmann

Balwant Singh

Steven L Peake

Arnold Zweig

Robert J Proverb

Jack K Siddens

Robert G Fischer

James S Farina

James Salvatore

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 tetramisole, dl-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazole, and its derivatives. The compound tetramisole is useful as an anthelmintic.

Synthesis of intermediates for tetramisole, levamisole and their

This disclosure describes a novel process for the preparation of 2-(n-propyl)-4-methyl-5-(lower alkanoyl)imidazoles which are useful as intermediates for the preparation of anti-asthmatic agents.

Process for preparing

This disclosure describes a novel process for the preparation of 1-(lower alkyl)substituted derivatives of 6-n-propyl-8-alkylimidazo[1,5-d]-as-triazin-4(3H)-ones which are useful as anti-asthmatic agents.

Process for preparing 5-imidazolyl ketones

This disclosure describes continuous epimerization-crystallization process for the isolation of [S-(R*, S*)]-1-(3-acetylthio-3-benzoyl-2-methylpropionyl)-L-proline from a diasteromeric mixture thereof with [S-(R*, R*)]-1-(3-acetylthio-3-benzoyl-2-methylpropionyl)-L-proline.

Isolation of [S-(R*,

Processes for reacting arylvinyl oxides and alkoxyethylamines to provide novel N-substituted alkoxyethylamines; processes for reacting the novel N-substituted amines with nitriles to provide novel amidoamines; processes for preparing novel diamines from the amidoamines, together with the novel nitrogen-containing products so produced, such products being useful for the preparation of various imidazothiazoles including tetramisole.

Amido methoxyethylamines

A method for the preparation of certain difluoromethoxyaromatic compounds useful as intermediates in the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent or solvent mixtures.

Method for the preparation of difluoromethoxyaromatic compounds

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]thiazols, 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.

Synthesis of tetramisole, levamisole and their derivatives

There is provided a process for racemizing an undesirable, optically active compound for conversion to levamisole, namely, l-N-(2-amino-2-phenethyl)-2-methoxyethylamine, by converting the latter to optically active l-(2-methoxyethyl)-4-phenyl-2-imidazolidone, which is next converted to the corresponding optically inactive imidazolidone derivative, which derivative is hydrolyzed to the optically inactive racemate, dl-N-(2-amino-2-phenethyl)-2-methoxyethylamine. The latter can be resolved to obtain the d and l components of the racemate, the d component being utilized directly in levamisole synthesis and the l component being again subjected to the above procedure.

Process for converting optically active

Processes for reacting aryl vinyl compounds, nitriles, and halogens to provide imidoyl halides; processes for preparing amidine hydrohalides from the imidoyl compounds; processes for producing novel imidazolines from the amidine hydrohalides; processes for preparing novel amidoamines from the imidazolines; processes for preparing novel diamines from the amidoamines, together with novel nitrogen-containing products so produced, such products being useful for the production of various imidazothiazoles including tetramisole.

1-(2-Methoxyethyl)-2-methyl-4-phenyl-2-imidazoline

Novel methoxyethylamine

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.

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 tetramisole, di-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazole, and its derivatives. The compound tetramisole is useful as an anthelmintic.

Growing community of inventors

Norwalk, CT, United States of America

Sivaraman Raghu