Verfahren zur Herstellung von Urethanen

• Main Author: MERTEN RUDOLF
• Format: Patent
• Language: German
• Published: 05.12.1963
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

The invention comprises cyclic urethanes of the formula:-<FORM:1001492/C2/1> wherein R is an unsubstituted or substituted alkyl, alkenyl, aryl, aralkyl, alkaryl, cycloalkyl or furfuryl radical, R1 is a hydrogen atom, an aralkenyl radical, a benzoyl radical, a heterocyclic radical other than furfuryl or a radical with the same meaning as R, and X is =C< or an oxygen atom. The radicals R and R1 may be further substituted for example by chlorine, nitro, cyano, acyloxy, alkoxy and dialkylamino, and the free bonds in the formula may be satisfied by further fused-on rings. The above urethanes are prepared by reacting a alkylidene-diurethane of the formula:- R1-CH(NH.COOR)2, or a condensation product produced from a non-basic aldehyde of the formula R1-CHO and a carbamic acid of the formula H2N.COOR in the presence of an acidic catalyst with a conjugated diolefin containing the structure <FORM:1001492/C2/2> or with an a ,b -unsaturated aldehyde or ketone containing the conjugated structure <FORM:1001492/C2/3> in the presence of an acidic catalyst. If a basic aldehyde is used to prepare the diurethane starting material it should be in the form of a salt. The diolefin and aldehyde or ketone reactants may be linear, cyclic or partly cyclic in nature and include a -phellandrene, 1,11-bicycloalkenyls, 1-alkenylcycloalkenes, 1,2 - dimethylene cycloalkenes, furans, cyclopentadienones, acrolein, vinyl methyl ketone, ortho-methylene cyclohexanone, ortho- - quinone - methidene, 2,21 - bis - 3 - indolonyl, vinyl pyridines, vinyl quinolines and abeitic acid.ALSO:An insecticidal composition comprises an aqueous emulsion of a compound of the formula <FORM:1001492/A5-A6/1>