Methylamine → HCID 10741054, compound

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Cl[S:24]([OH:27])(=O)=[O:25].[CH3:28][NH2:29]>O1CCCC1>[CH3:28][NH:29][S:24]([C:10]1[S:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:11]=1)(=[O:27])=[O:25]

Participants

Procedure

2-(4-Fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (1.1 g) was added portionwise to chlorosulfonic acid (1 ml), and the mixture was stirred at ambient temperature for 1 hour. The mixture was added to a mixture of 25% methylamine aqueous solution (20 ml) and tetrahydrofuran (20 ml), and stirred at 0° C. for 1 hour. The reaction mixture was extracted with ethyl acetate, and the extract was washed with water, dried and concentrated. The oily residue (2.4 g) was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1), and then recrystallized from ethanol to give colorless crystals of N-methyl-5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-sulfonamide (1.1 g).