Triethylamine → HCID 22152627, compound

Participants

Reaction Steps

To prepare the starting material, acetaldehyde 4-chloro-3-methylsulfonylaminophenylhydrazone, a mixture of 20.0 5 (116 mmoles) of 2-chloro-5-nitroaniline (compound 4, FIG. 1), 24.6 g (243 mmoles) of triethylamine and 100 ml of methylene chloride was cooled in an ice bath, and a solution of 27.8 g (243 mmols) of methylsulfonyl chloride in 20 ml of methylene chloride was added dropwise. When the addition was about half complete the ice bath was removed. After completion of the addition, the mixture was allowed to stand for an hour and then filtered to remove undesired salts. The filtrate was evaporated under reduced pressure to give a yellow solid which was washed with 100 ml of water; the filter cake was then mixed with 100 ml of ethanol and then filtered rapidly, and the resulting off-white solid was dried in vacuo to give 32.7 g of 2-chloro-5-nitro-1-bis(methylsulfonyl)amino-benzene. The latter was then mixed with 50 ml of ethanol; 8 g of NaOH in 20 ml of water was added slowly with stirring, after which the mixture was diluted with 300 ml of water followed by the addition of 45 ml of 6N HCl, yielding a precipitate which was collected by filtration and dried in vacuo to give 24.3 g of 2-chloro-5-nitro-1-methylsulfonylaminobenzene (compound 4, FIG. 1). The latter material was reduced with iron powder to form 17.7 g of 4-chloro-3-methylsulfonylaminoiline.

Provenance & Evidence