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US4054585A
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Furan-3-carboxamide derivatives and method of preparing same
Assignee: Uniroyal Chemical Co Inc
•
Filing: 1976-06-09
•
Granted: 1977-10-18
•
Expires: 1996-06-09
Abstract
Abstract A broad class of furan-3-Carboxamide derivatives, including many novel compounds, can be made reliably and in good yields by a novel one step reaction between an α-hydroxyketone and an acetamide in the presence of a Friedel-Crafts agent in an inert solvent. The broad class of derivatives has fungicidal and insecticidal utility.
Inventors
- 👤 Ethel E. Felauer
- 👤 Marshall Kulka
- 👤 Bogislav von Schmeling
- 👤 Robert A. Davis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 01:19
CPC Classifications
A; A01; A01N; A01N43/00; A01N43/72; A01N43/74; A01N43/78; A01N43/02; A01N43/04; A01N43/06; A01N43/08; C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68; C07D307/77; C07D307/78; C07D307/82; C07D307/84
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
164 words
A compound having the structural formula ##STR31## wherein R is hydrogen, alkyl of 1 to 2 carbon atoms, benzoyl, or trichloromethylsulfenyl; R 1 is phenyl, alkylphenyl, alkoxyphenyl, halophenyl, nitrophenyl, benzyl, biphenylyl, alkyl having from 1 to 10 carbon atoms, allyl, cyclohexyl, naphthyl, pyridyl, thiazolyl, ethylene bis-, or furfuryl; or R and R 1 taken together are oxydiethylene; Y and Z are independently selected from the group consisting of hydrogen, halo, amino, alkyl having 1 to 17 carbon atoms, hydroxyalkyl of 1 to 17 carbon atoms, chloroalkyl of 1 to 17 carbon atoms, nitroalkyl of 1 to 17 carbon atoms, allyl, phenyl, alkylphenyl, alkoxyphenyl, halophenyl, or Y and Z together are, alkylene; and X is either alkyl having from 1 to 17 carbon atoms or phenyl; provided that if ______________________________________
if (R is H )
(R.sub.1
is phenyl )
(X is CH.sub.3
)
(Z is H ) , then Y is not H or CH.sub.3.
______________________________________ then Y is not H or CH 3 .
Claim 2
Dependent Claim
164 words
A compound having the structural formula ##STR31## wherein R is hydrogen, alkyl of 1 to 2 carbon atoms, benzoyl, or trichloromethylsulfenyl; R 1 is phenyl, alkylphenyl, alkoxyphenyl, halophenyl, nitrophenyl, benzyl, biphenylyl, alkyl having from 1 to 10 carbon atoms, allyl, cyclohexyl, naphthyl, pyridyl, thiazolyl, ethylene bis-, or furfuryl; or R and R 1 taken together are oxydiethylene; Y and Z are independently selected from the group consisting of hydrogen, halo, amino, alkyl having 1 to 17 carbon atoms, hydroxyalkyl of 1 to 17 carbon atoms, chloroalkyl of 1 to 17 carbon atoms, nitroalkyl of 1 to 17 carbon atoms, allyl, phenyl, alkylphenyl, alkoxyphenyl, halophenyl, or Y and Z together are, alkylene; and X is either alkyl having from 1 to 17 carbon atoms or phenyl; provided that if ______________________________________
if (R is H )
(R.sub.1
is phenyl )
(X is CH.sub.3
)
(Z is H ) , then Y is not H or CH.sub.3.
______________________________________ then Y is not H or CH 3 .
Claim 3
Dependent Claim
143 words
The compound of claim 1, wherein R is hydrogen, alkyl having 1 to 2 carbon atoms, benzoyl, or trichloromethylsulfenyl; R 1 is phenyl, a methyl-substituted phenyl, methoxyphenyl fluorophenyl, a chloro-substituted phenyl, nitrophenyl, benzyl, biphenylyl, alkyl having 1 to 10 carbon atoms, allyl, cyclohexyl, naphthyl, pyridyl, thiazolyl, ethylene bis-, or furfuryl; or R and R 1 taken together are oxydiethylene; Y is hydrogen, alkyl having 1 to 3 carbon atoms, or hydroxymethyl; Z is hydrogen, alkyl having 1 to 4 carbon atoms, or phenyl; or Y and Z taken together are tetramethylene; and X is either alkyl having 1 to 17 carbon atoms or phenyl; provided that if ______________________________________
if (R is H )
(R.sub.1
is phenyl )
(X is CH.sub.3
)
(Z is H ) , then Y is not H or CH.sub.3.
______________________________________ then Y is not H or CH 3 .
Claim 4
Dependent Claim
10 words
The compound of claim 1, wherein R 1 is cyclohexyl.
Claim 5
Dependent Claim
9 words
The compound of claim 3, wherein R is hydrogen.
Claim 6
Dependent Claim
10 words
The compound of claim 1, wherein R 1 is phenyl.
Claim 7
Dependent Claim
9 words
The compound of claim 5, wherein R is hydrogen.
Claim 8
Dependent Claim
22 words
The compound of claim 1, wherein R is hydrogen, R 1 is cyclohexyl, X is methyl, and Y and Z are hydrogen.
Claim 9
Dependent Claim
22 words
The compound of claim 1, wherein R is hydrogen, R 1 is cyclohexyl, and each of X, Y and Z is methyl.
Claim 10
Dependent Claim
22 words
The compound of claim 1, wherein R is hydrogen, R 1 is o-methylphenyl, X is methyl, and Y and Z are hydrogen.
Claim 11
Dependent Claim
22 words
The compound of claim 1, wherein R is hydrogen, R 1 is o-methylphenyl, and each of X, Y and Z is methyl.
Claim 12
Dependent Claim
22 words
The compound of claim 1, wherein R is hydrogen, R 1 is m-methylphenyl, X is methyl, and Y and Z are hydrogen.
Claim 13
Dependent Claim
22 words
The compound of claim 1, wherein R is hydrogen, R 1 is m-methoxyphenyl, X is methyl, and Y and Z are hydrogen.
Claim 14
Dependent Claim
22 words
The compound of claim 1, wherein R is hydrogen, R 1 is p-methoxyphenyl, and each of X, Y and Z is methyl.
Claim 15
Dependent Claim
1 words
2,4,5-trimethylfuran-3-carboxanilide.
Claim 16
Dependent Claim
1 words
2,4,5-trimethylfuran-3-carboxanilide.
Claim 17
Dependent Claim
1 words
2,5-dimethylfuran-3-carboxanilide.
Claim 18
Dependent Claim
1 words
2,5-dimethylfuran-3-carboxanilide.
Claim 19
Independent Claim
180 words
A method of making a compound of the formula: ##STR32## wherein X, Y and Z are independently selected from the group consisting of hydrogen, alkyl containing 1 to 17 carbon atoms, lower hydroxyalkyl, allyl, phenyl, lower alkoxyphenyl, lower alkylphenyl, nitrophenyl and halophenyl, or Y and Z together are 1,4-butylene; R is selected from the group consisting of hydrogen, alkyl containing 1 to 10 carbon atoms, benzoyl and trichloromethyl sulfenyl; and R 1 is selected from the group consisting of phenyl, lower alkylphenyl, lower alkoxyphenyl, halophenyl, nitrophenyl, benzyl, biphenylyl, alkyl containing 1 to 10 carbon atoms, allyl, cyclohexyl, naphthyl, pyridyl, thiazolyl, ethylene bis-, and furfuryl, or R and R 1 together with the nitrogen is morpholino, said method comprising reacting an alphahydroxyketone or aldehyde of the formula ##STR33## with an acetamide of the formula ##STR34## where X, Y, Z, R and R 1 have the meanings set forth above in this claim, in an inert, non-hydroxylic solvent and in the presence of an active Friedel-Crafts reagent selected from the group consisting of AlCl 3 , AlBr 3 and SnCl 4 .
Claim 20
Dependent Claim
37 words
The method of claim 16 wherein about equimolar amounts of said alpha-hydroxyketone or aldehyde and acetamide are used, and about 0.5 mole of said Friedel-Crafts reagent is present for each mole of alpha-hydroxyketone or aldehyde or acetamide.
Claim 21
Dependent Claim
49 words
The method of claim 16 wherein about equimolar amounts of said alpha-hydroxyketone or aldehyde and acetamide are used and about 0.01 to 0.5 mole of said Friedel-Crafts reagent is present for each mole of alpha-hydroxyketone or aldehyde or acetamide, together with means for removing water formed by the reaction.
Claim 22
Independent Claim
40 words
The method of producing 2,4,5-trimethylfuran-3-carboxanilide which comprises reacting acetoin with acetoacetanilide in an inert, non-hydroxylic solvent and in the presence of an active Friedel-Crafts reagent selected from the group consisting of AlCl 3 , AlBr 3 and SnCl 4 .
Claim 23
Independent Claim
40 words
The method of producing 2,4,5-trimethylfuran-3-carboxanilide which comprises reacting acetoin with acetoacetanilide in an inert, non-hydroxylic solvent and in the presence of an active Friedel-Crafts reagent selected from the group consisting of AlCl 3 , AlBr 3 and SnCl 4 .
Claim 24
Independent Claim
40 words
The method of producing 2,4,5-trimethylfuran-3-methylcarboxanilide which comprises reacting acetoin with methylacetoacetanilide in an inert, non-hydroxylic solvent and in the presence of an active Friedel-Crafts reagent selected from the group consisting of AlCl 3 , AlBr 3 and SnCl 4 .
Claim 25
Independent Claim
40 words
The method of producing 2,4,5-trimethylfuran-3-methylcarboxanilide which comprises reacting acetoin with methylacetoacetanilide in an inert, non-hydroxylic solvent and in the presence of an active Friedel-Crafts reagent selected from the group consisting of AlCl 3 , AlBr 3 and SnCl 4 .
Claim 26
Independent Claim
40 words
The method of producing 2,4,5-trimethylfuran-3-methoxycarboxanilide which comprises reacting acetoin with methoxyacetoacetanilide in an inert, non-hydroxylic solvent and in the presence of an active Friedel-Crafts reagent selected from the group consisting of AlCl 3 , AlBr 3 and SnCl 4 .
Claim 27
Independent Claim
40 words
The method of producing 2,4,5-trimethylfuran-3-methoxycarboxanilide which comprises reacting acetoin with methoxyacetoacetanilide in an inert, non-hydroxylic solvent and in the presence of an active Friedel-Crafts reagent selected from the group consisting of AlCl 3 , AlBr 3 and SnCl 4 .
References Cited (Backward Citations)
US3352663A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-10-17 | 1981-04-18 | 1981-10-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-17 | 1985-04-18 | 1985-10-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-17 | 1989-04-18 | 1989-10-18 | $7700.00 | Window Closed / Lapsed |