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US4013684A
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Preparation of 2,5-dimethylfuran-3-carboxylic amides
Assignee: BASF SE
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Filing: 1973-05-14
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Granted: 1977-03-22
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Expires: 1993-05-14
Abstract
Abstract New and valuable process for the production of 2,5-dimethylfuran-3-carboxylic amides by reaction of acyloxypropionaldehyde with acetoacetamide.
Inventors
- 👤 Hans Rupert Merkle
- 👤 Hardo Siegel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 00:28
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68; A; A01; A01N; A01N43/00; A01N43/02; A01N43/04; A01N43/06; A01N43/08
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
109 words
A process for the production of a 2,5-dimethylfurancarboxylic amide of the formula ##EQU5## where R 1 and R 2 are identical or different and each denotes hydrogen, phenyl, substituted phenyl, cycloalkyl, substituted cyclohexyl, alkenyl, cycloalkenyl, alkynyl, bicycloalkyl or alkyl of 1 to 4 carbon atoms, wherein an α-acyloxypropionaldehyde of the formula ##EQU6## where ac denotes formyl, acetyl, propionyl, butyryl or isobutyryl, is reacted with an acetoacetamide of the formula ##EQU7## where R 1 and R 2 have the above meanings, in the presence of 0.005 to 25% by weight, with reference to the α-acyloxypropionaldehyde, of an acid catalyst selected from the group consisting of sulfuric acid and p-toluenesulfonic acid.
Claim 2
Dependent Claim
109 words
A process for the production of a 2,5-dimethylfurancarboxylic amide of the formula ##EQU5## where R 1 and R 2 are identical or different and each denotes hydrogen, phenyl, substituted phenyl, cycloalkyl, substituted cyclohexyl, alkenyl, cycloalkenyl, alkynyl, bicycloalkyl or alkyl of 1 to 4 carbon atoms, wherein an α-acyloxypropionaldehyde of the formula ##EQU6## where ac denotes formyl, acetyl, propionyl, butyryl or isobutyryl, is reacted with an acetoacetamide of the formula ##EQU7## where R 1 and R 2 have the above meanings, in the presence of 0.005 to 25% by weight, with reference to the α-acyloxypropionaldehyde, of an acid catalyst selected from the group consisting of sulfuric acid and p-toluenesulfonic acid.
Claim 3
Dependent Claim
17 words
A process as claimed in claim 1 wherein the reaction is carried out at -10° to +180°C.
Claim 4
Dependent Claim
17 words
A process as claimed in claim 1 wherein R 1 is phenyl and R 2 is hydrogen.
Claim 5
Dependent Claim
17 words
A process as claimed in claim 1 wherein R 1 is cyclohexyl and R 2 is hydrogen.
References Cited (Backward Citations)
US3806506A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-03-21 | 1980-09-20 | 1981-03-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-21 | 1984-09-20 | 1985-03-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-21 | 1988-09-20 | 1989-03-22 | $7700.00 | Window Closed / Lapsed |