CA1176659A - Process for producing n-substituted-n-acetyl-2,6- dialkylanilines - Google Patents

Abstract

Case 5-12314/+

Process for producing N-substituted-N-acetyl-2,6-dialkylanilines Abstract of the Disclosure A process for producing N-substituted-N-acetyl-2,6-dialkylanilines of the formula in which R1 and R2 independently of one another are each methyl or ethyl, A is a 1,2- ethylene group which can be substituted by 1 or 2 methyl groups, a 2-oxo-1,2-ethylene group or a 1-methyl-2-oxo-1,2 ethylene group, R3 is an alkyl group having 1 to 3 carbon atoms, and X represents chlorine or an alkoxy group having 1 to 3 carbon atoms, is disclosed, which process comprises reacting a N-substituted-2,6-dialkylaniline of the formula in which R1, R2, R3 and A have the meaning given above with an acetyl chloride of the formula X - CH2 - CO - Cl in which X has the meaning given above, in an excess of said acetyl chloride as solvent.

The N-substituted-N-acetyl-2,6-dialkylanilines of the above formula can be used for protecting plants from being infected by phyto-pathogenic microorganisms.

Claims (7)

What is claimed is:

1. Process for producing N-substituted-N-acetyl-2,6-dialkylanilines of the formula I
(I) in which R1 and R2 independently of one another are each methyl or ethyl, A is a 1,2-ethylene group which can be substituted by 1 or 2 methyl groups, a 2-oxo-1,2-ethylene group or a 1-methyl-2-oxo-1,2-ethylene group, R3 is an alkyl group having 1 to 3 carbon atoms, and X represents chlorine or an alkoxy group having 1 to 3 carbon atoms, which comprises reacting a N-substituted-2,6-dialkylaniline of the formula II
(II) in which R1, R2, R3 and A are as defined under the formula I, with an acetyl chloride of the formula III
X - CH2 - CO - Cl (III) in which X is as defined under formula I, in the presence of excess acetyl chloride of the formula III as solvent, distilling of the excess acetyl chloride of the formula III, washing the formed N-substituted-N-acetyl-2,6-dialkylaniline of the formula I with water until neutral, and subsequently drying the product.

2 A process according to claim 1, wherein 2 to 20 mols of acetyl chloride of the formula III are used per mol of N-substituted-2,6-dialkylaniline of the formula II.

3. A process according to claim 1, wherein 4 to 8 mols of acetyl chloride of the formula III are used per mol of N-substituted-2,6-di-alkylaniline of the formula II.

4. A process according to Claim 1, wherein the reaction of N-sub-stituted-2,6-dialkylaniline of the formula II with the acetyl chloride of the formula III is performed in the temperature range of 70°C to the reflux temperature of the reaction mixture.

5. A process according to Claim l, wherein the reaction of N-substituted-2,6-dialkylaniline of the formual II with the acetyl chloride of the formula III is performed at the reflux temperature of the reaction mixture.

6. A process according to Claim l, wherein the N-substituted -N-acetyl-2,6-dialkylaniline of the formula I, obtained after re-moval by distillation of the excess acetyl chloride of the formula III, is washed at 50 to 100°C with water.

7. A process according to claims 1 and 6, wherein there is added to the washing water an amount of alkali sufficient to bring the pH value of the water to 4 to 10.