Dialkyl acetals of anilinoacetaldehydes

#This invention relates to new compositions of matter and more specifically relates to new chemical compounds of the formula ##STR2## wherein R.sup.1, R.sup.6 and R.sup.7 are each alkyl; R.sup.2 is selected from the group consisting of hydrogen, alkyl, alkoxy and trifluoromethyl; R.sup.3 and R.sup.4 are each selected from the group consisting of hydrogen, lower alkyl, halogen, cyano, alkoxy, alkylthio, haloalkyl and alkoxyalkyl; R.sup.5 is selected from the group consisting of hydrogen and alkyl; and X is halogen.

#The compounds of the present invention are unexpectedly useful as herbicides.

#In a preferred embodiment of this invention R.sup.1, R.sup.6 and R.sup.7 are each lower alkyl; R.sup.2 is selected from the group consisting of hydrogen, lower alkyl and lower alkoxy; R.sup.3 and R.sup.4 are each selected from the group consisting of hydrogen, lower alkyl, halogen, cyano, lower alkoxy, lower alkylthio, lower chloroalkyl, trifluoromethyl and lower alkoxyalkyl; R.sup.5 is selected from the group consisting of hydrogen and lower alkyl; and X is selected from the group consisting of chlorine and bromine.

#2,6-Dimethylaniline (60 grams), the dimethyl acetal of 2-chloroacetaldehyde (25 grams) and sodium carbonate (21.2 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at 150.degree. C. for a period of about 30 hours. After this time the mixture was filtered and the filtrate was distilled to yield the desired product the dimethyl acetal of 2-(2,6-dimethylanilino)acetaldehyde having a boiling point of 105.degree. C. at 1 mm of Hg pressure.

#The dimethyl acetal of 2-(2,6-dimethylanilino)-acetaldehyde (12.2 grams), triethylamine (8.1 ml) and benzene (50 ml) were charged into a reaction vessel equipped with a mechanical stirrer, thermometer and cooling means. The mixture was cooled to about 0.degree. C. and chloroacetyl chloride (4.4 ml) was incrementally added with stirring. After the addition was complete stirring was continued and the reaction mixture was permitted to warm to room temperature. After this time the mixture was filtered, washed with dilute hydrochloric acid and stripped of solvent under reduced pressure to yield the desired product the dimethyl acetal of 2-(N-.alpha.-chloroacetyl-2,6-dimethylanilino)acetaldehyde.

#2,6-Diethylaniline (120 grams), the diethyl acetal of 2-chloroacetaldehyde (78.8 grams) and sodium carbonate (42.4 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at 150.degree. C. for a period of about 30 hours. After this time the mixture was filtered and the filtrate was distilled to yield the desired product the diethyl acetal of 2-(2,6-diethylanilino)acetaldehyde having a boiling point of 130.degree. C. at 1 mm of Hg pressure.