4-Chloroaniline → HCID 57426257, compound

Participants

Reaction Steps

Ten grams (0.05 mole) of bis(ethylsulfonyl)methane, prepared by the procedure described in Cronyl "Sulfones. I. Methods for the Preparation of Certain Alkanes, Alkenes, Acids and Lactones with Bis-(ethylsulfonyl)-methane" in J. Am. Chem. Soc., vol. 74, page 1225 (see p. 1228), published 1952, was mixed with 7.4 grams (0.05 mole) of ethyl orthoformate and 6.4 grams (0.05 mole) of p-chloroaniline and the mixture was heated at 95°-145°C. (pot) during which time about 7 milliliters of ethanol distilled off. The reaction mixture was then further heated at 150°-160°C. for 1 hour and then cooled. The solid reaction product was then washed with cold ethanol, and recrystallized from ethanol to give 7.3 grams of 2,2-bis(ethylsulfonyl)vinyl-4-chloroaniline, melting point 173°-175°C. having the structural formula ##SPC5##

Provenance & Evidence