J. Gardner, R. Y. Moir, C. Purves
Sep 1, 1948
Citations
0
Influential Citations
2
Citations
Journal
Canadian journal of research
Abstract
The object of the work was to prepare alkoxylated derivatives of sym-diethyldiphenylurea from methylated and ethylated vanillin. Standard procedures for converting methylated vanillin to 3,4-dimethoxyaniline were extended to the syntheses of the known 3-methoxy-4-ethoxyaniline. The following derivatives of 3,4-dimethoxyaniline are believed to be new: the formanilide, m.p. 91 °C.; sulphonamide, m.p. 132 °C.; N-ethylsulphonamide, m.p. 94 °C.; N-ethylacetanilide, m.p. 62 °C.; and the N-ethylaniline, an uncrystallized oil. Condensations of the last with phosgene yielded the N-ethylcarbamyl chloride, m.p. 86 °C.; N-ethyl-NN'-NN′-(3,4-dimethoxyphenyl)-urea, m.p. 159 °C.; and the corresponding sym-N,N′-diethyl derivative, m.p. 79 °C. N,N′-di-(3,4-dimethoxyphenyl)-urea, m.p. 214 °C., was synthesized by a method that removed previous doubt about its structure. The derivatives of 3-methoxy-4-ethoxyaniline believed to be new are: the hydrochloride, m.p. 221 °C.; the formanilide, m.p. 103 °C.; the N-ethylformanilide,...