Prepd. of antimicrobial alkyl-acylate cpds. - by reacting sulphide cpd. with fuming nitric acid

摘要

Prepn. of alkylacrylates of formula Ar1ZCHR1CHAr2OCOR2 (I) comprises reaction of a sulphide of formula Ar1ZCHR1CHAr2SR5 (II) with an excess of fuming nitric acid, in an acid anhydrides at -15 to -20 deg.C. In the formulae, Ar = phenyl or pyridyl (both substd. by 1-4 R3 gps.), or thienyl or furyl (both substd. by 1-3 R4 gps.); R3 = H, halo, halo(1-6C)alkyl (esp. CF3 or CCl3), CN, NO2, OH, 1-6C alkyl, 3-6C cycloalkyl, 1-6C alkoxy, or phenoxy, phenyl or phenyl (1-6C) alkyl (themselves opt. ring substd. by 1-3 halo); R4 = H, halo or 1-6C alkyl; Z = CO, N-aryl(Ar1)-carbamoyl, oxycarbonyl, SO2, NO2 or CN; R1 = H, 1-6C alkyl, phenyl, 2-naphthyl, 2-thienyl, 2-furyl, 2-pyridyl or 3-pyridyl; Ar2 = a gp. R3; R2 = 1-6C alkyl; R5 = cyclohexyl, triphenylmethyl, phenyl, 4-chlorophenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl- or 4-aminophenyl. Provided that when Z is NO2 or CN, the gp. Ar1 is absent. USE/ADVANTAGE - (I) are useful as antimicrobial agents. The process is quick, easy and economical.