Furan-3-carboxamide derivatives and method of preparing same
AssigneeUniroyal, Inc.
InventorsEthel E. Felauer, Marshall Kulka, Bogislav Von Schmeling, Robert A. Davis
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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 .alpha.-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.
Claims21
A compound having the structural formula ##STR31## wherein R is hydrogen, alkyl of 1 to 2 carbon atoms, benzoyl, or trichloromethylsulfenyl;
- R.sub.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.sub.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.sub.3.
2,4,5-trimethylfuran-3-carboxanilide.
2,5-dimethylfuran-3-carboxanilide.
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.sub.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.sub.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.sub.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.sub.3, AlBr.sub.3 and SnCl.sub.4.
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.sub.3, AlBr.sub.3 and SnCl.sub.4.
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.sub.3, AlBr.sub.3 and SnCl.sub.4.
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.sub.3, AlBr.sub.3 and SnCl.sub.4.
Dependencies are inferred from the claim text.