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EP0106962A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Process for preparing 4(or 5)-(1-hydroxyalkyl) imidazoles

Assignee: Wyeth Holdings LLC
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Filing: 1983-08-13
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Granted: —
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Expires: 2003-08-13
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Abstract

Abstract A process is disclosed for preparing a compound of the formula wherein R, and R 3 are the same or a different straight or branched chain lower alkyl group; and R 2 is hydrogen, a straight or branched chain lower alkyl, benzyl, or phenyl group, or a phenyl group substituted with a halo, a straight or branched chain lower alkyl or alkoxy, an amino, a lower dialkylamino or a nitro group The process comprises adding a compound of the formula to an aqueous solution of an acid to form a reaction mixture, the mole ratio of the acid to formula (II) being about 1.75 to 2.5; maintaining the reaction mixture at a temperature of about 85 to 95°C for about 1 to 3 hours; neutralizing the reaction mixture; recovering the precipitate effected by the neutralizing step; and separating from the precipitate the compound of formula (I). The compounds 4 (or 5)-methyl-5 (or 4)-ethyl-2-propyl-2-imidazoline-4, 5-diol hydrochloride (or 4), and 4 (or 5)-methyl-2,5 (or 2,4)-di-n-propyl-2-imidazoline-4,5-diol are also disclosed.

Inventors

  • 👤 Thurairajah Padmanathan

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-09 08:12
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 144 words
A process for preparing a compound of the formula wherein R 1 and R 3 are the same or a different straight or branched chain lower alkyl group; and R 2 is hydrogen, a straight or branched chain lower alkyl, benzyl, or phenyl group, or a phenyl group substituted with a halo, a straight or branched chain lower alkyl or alkoxy, an amino, a lower dialkylamino or a nitro group, comprising: adding a compound of the formula to an aqueous solution of an acid to form a reaction mixture, the mole ratio of said acid to said formula (II) being about 1.75 to 2.5; maintaining said reaction mixture at a temperature of about 85 to 95°C for about 1 to 3 hours; neutralizing said reaction mixture; recovering the precipitate effected by said neutralizing step; and separating from said precipitate the compound of formula (I).
Claim 2
Dependent Claim 144 words
A process for preparing a compound of the formula wherein R 1 and R 3 are the same or a different straight or branched chain lower alkyl group; and R 2 is hydrogen, a straight or branched chain lower alkyl, benzyl, or phenyl group, or a phenyl group substituted with a halo, a straight or branched chain lower alkyl or alkoxy, an amino, a lower dialkylamino or a nitro group, comprising: adding a compound of the formula to an aqueous solution of an acid to form a reaction mixture, the mole ratio of said acid to said formula (II) being about 1.75 to 2.5; maintaining said reaction mixture at a temperature of about 85 to 95°C for about 1 to 3 hours; neutralizing said reaction mixture; recovering the precipitate effected by said neutralizing step; and separating from said precipitate the compound of formula (I).
Claim 3
Dependent Claim 17 words
A process of Claim 1 wherein R1 and R 3 are methyl, and R 2 is n-propyl.
Claim 4
Dependent Claim 17 words
A process of Claim 1 wherein R1 and R 3 are methyl, and R 2 is phenyl.
Claim 5
Dependent Claim 19 words
A process of Claim 1 wherein R 1 is methyl, R 2 is propyl and R 3 is ethyl.
Claim 6
Dependent Claim 27 words
A process of Claim 1 or 2 or 3 or 4 wherein said acid is selected from the group consisting of hydrochloric, sulfuric, phosphoric, boric and p-toluenesulfonic.
Claim 7
Dependent Claim 11 words
A process of Claim 5 wherein said acid is hydrochloric acid.
Claim 8
Dependent Claim 21 words
A process of Claim 6 wherein the mole ratio of said acid to said formula (II) is about 1.9 to 2.2.
Claim 9
Dependent Claim 20 words
A process of Claim 7 wherein said reaction mixture is maintained at about 90 to 92°C for about one hour.
Claim 10
Dependent Claim 10 words
The compound 4 (or 5)-methyl-5 (or 4)-ethyl--2-propyl-2-imidazoline-4,5-diol hydrochloride (or 4).
Claim 11
Dependent Claim 10 words
The compound 4 (or 5)-methyl-5 (or 4)-ethyl--2-propyl-2-imidazoline-4,5-diol hydrochloride (or 4).
Claim 12
Dependent Claim 7 words
The compound 4 (or 5)-methyl-2,5 (or 2,4)--di-n-propyl-2-imidazoline-4,5-diol.
Claim 13
Dependent Claim 7 words
The compound 4 (or 5)-methyl-2,5 (or 2,4)--di-n-propyl-2-imidazoline-4,5-diol.

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