Methanesulfonamide → N-(4-hexadecylamino-2-thiophenecarbonyl)methanesulfonamide
Reaction equation
Cl.[CH2:2]([NH:18][C:19]1[CH:20]=[C:21]([C:24](Cl)=[O:25])[S:22][CH:23]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH3:27][S:28]([NH2:31])(=[O:30])=[O:29]>N1C=CC=CC=1>[CH2:2]([NH:18][C:19]1[CH:20]=[C:21]([C:24]([NH:31][S:28]([CH3:27])(=[O:30])=[O:29])=[O:25])[S:22][CH:23]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 25 g. of 4-hexadecylamino-2-thiophenecarbonyl chloride hydrochloride and 5.6 g. of methanesulfonamide in 250 ml. of pyridine is stirred under reflux for 2 hours and then concentrated in vacuo. The residue is partitioned between water and diethyl ether; the aqueous layer acidified with 1 N hydrochloric acid and the organic layer seperated, dried over magnesium sulfate, and evaporated. Crystallization of the residual white solid from 60% aqueous acetic acid and then from methylene chloride-hexane affords the product as a white solid.