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1. WO2002040454 - PROCESS FOR MANUFACTURE OF IMIDAZOLES

Publication Number WO/2002/040454
Publication Date 23.05.2002
International Application No. PCT/US2000/031598
International Filing Date 16.11.2000
Chapter 2 Demand Filed 17.06.2002
IPC
C07D 521/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
521Heterocyclic compounds containing unspecified hetero rings
CPC
C07D 231/12
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
231Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
02not condensed with other rings
10having two or three double bonds between ring members or between ring members and non-ring members
12with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
C07D 233/56
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
233Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
54having two double bonds between ring members or between ring members and non-ring members
56with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
C07D 249/08
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
249Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
02not condensed with other rings
081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Applicants
  • THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ALABAMA [US]/[US] (AllExceptUS)
  • ARDUENGO, Anthony, J., III [US]/[US] (UsOnly)
  • PRAKASHA, Taverekere, K. [US]/[US] (UsOnly)
  • GENTRY, Frederick, P., Jr. [US]/[US] (UsOnly)
  • SIMMONS, Howard, E., III [US]/[US] (UsOnly)
Inventors
  • ARDUENGO, Anthony, J., III
  • PRAKASHA, Taverekere, K.
  • GENTRY, Frederick, P., Jr.
  • SIMMONS, Howard, E., III
Agents
  • GOLIAN, Andrew, G.
Priority Data
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) PROCESS FOR MANUFACTURE OF IMIDAZOLES
(FR) PROCEDE DE FABRICATION D'IMIDAZOLES
Abstract
(EN)
Imidazoles may be manufactured by reacting a glyoxal, ammonia, an aldehyde, and optionally a primary amine, in the presence of a Bronsted acid whose pKa is approximately equal to the pKa of the ammonium cation of the primary amine, or if the primary amine is not present, to the pKa of the ammonium (NH4+) cation. The reaction may be used to make in relatively high yields a wide variety of imidazoles using relatively inexpensive starting materials. The imidazoles are useful as chemical intermediates. Formula (V) and formula (IX).
(FR)
Des imidazoles peuvent être fabriqués par réaction d'un glyoxal, d'ammoniac et d'un aldéhyde, et éventuellement d'une amine primaire, en présence d'un acide de Brönsted dont le pKa est approximativement égal au pKa du cation ammonium de l'amine primaire, ou, si l'amine primaire n'est pas présent, au pKa du cation ammonium (NH4+). La réaction peut être utilisée pour fabriquer à relativement haut rendement une large gamme d'imidazoles en utilisant des matières premières relativement bon marché. Les imidazoles sont utiles en tant que produits intermédiaires. Formule (V) et formule (IX).
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