US4063023A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing 4-(hydroxymethyl)imidazole compounds
Assignee: Sk&F Lab Co
•
Filing: 1976-05-27
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Granted: 1977-12-13
•
Expires: 1996-05-27
Abstract
Abstract An improved process for the preparation of 4-(hydroxymethyl)imidazoles by reducing 4-imidazolecarboxylic acid esters using an alkali metal or calcium in liquid ammonia with an additional proton source provided during the reaction or upon workup.
Inventors
- 👤 Elvin L. Anderson
- 👤 Wilford L. Mendelson
- 👤 George R. Wellman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 08:38
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
58 words
A process for the preparation of a 4-(hydroxymethyl)imidazole compound of the formula: ##STR2## in which R is hydrogen or lower alkyl, which comprises reducing a 4-imidazolecarboxylic acid ester of the formula: ##STR3## in which R is as defined above and R' is lower alkyl, using an alkali metal or calcium in liquid ammonia with an additional proton source.
Claim 2
Dependent Claim
58 words
A process for the preparation of a 4-(hydroxymethyl)imidazole compound of the formula: ##STR2## in which R is hydrogen or lower alkyl, which comprises reducing a 4-imidazolecarboxylic acid ester of the formula: ##STR3## in which R is as defined above and R' is lower alkyl, using an alkali metal or calcium in liquid ammonia with an additional proton source.
Claim 3
Dependent Claim
28 words
A process of claim 1 in which the additional proton source is present during the reaction of the ester with the alkali metal or calcium and liquid ammonia.
Claim 4
Dependent Claim
16 words
A process of claim 1 in which the 4-(hydroxymethyl)imidazole is isolated as an acid addition salt.
Claim 5
Dependent Claim
24 words
A process of claim 1 in which sodium in liquid ammonia is used and the additional proton source is a lower alkanol or cycloalkanol.
Claim 6
Dependent Claim
23 words
A process of claim 4 in which 5-methyl-4-imidazolecarboxylic acid lower alkyl ester and a lower alkanol are added to sodium in liquid ammonia.
Claim 7
Dependent Claim
30 words
A process of claim 1 in which at least four equivalents of the alkali metal or two equivalents of calcium are present for each equivalent of the 4-imidazolecarboxylic acid ester.
Claim 8
Dependent Claim
12 words
A process of claim 1 in which an alkali metal is used.
Claim 9
Dependent Claim
12 words
A process of claim 7 in which the alkali metal is sodium.
Claim 10
Dependent Claim
10 words
A process of claim 1 in which R is methyl.
Claim 11
Dependent Claim
12 words
A process of claim 9 in which R' is methyl or ethyl.
Claim 12
Dependent Claim
24 words
A process of claim 10 in which sodium in liquid ammonia is used and the additional proton source is a lower alkanol or cycloalkanol.
References Cited (Backward Citations)
DE2211454A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-12-12 | 1981-06-13 | 1981-12-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-12 | 1985-06-13 | 1985-12-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-12 | 1989-06-13 | 1989-12-13 | $7700.00 | Window Closed / Lapsed |