4-Chlorobenzenesulfonyl chloride → HCID 13280086, compound
Reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[CH3:15])=[O:5].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>N1C=CC=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:1][C:2]2[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=2[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH3:15])=[O:5])(=[O:29])=[O:28])=[CH:23][CH:22]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Amino-N-[3-(2-methylimidazol-1-yl)propyl]benzamide (10.5 g) was dissolved in pyridine (50 ml) and 4-chlorobenzenesulphonyl chloride (12.35 g) was added in portions during five minutes. The temperature of the reaction mixture rose to 45° C. The solution was stirred at room temperature for 4 hours and the pyridine was evaporated in vacuo to give a brown oil. The oil was chromatographed on silica gel, eluting with a mixture of chloroform and methanol (19:1) to give 2-(4-chlorobenzenesulphonamido)-N-[3-(2-methylimidazol-1-yl)propyl]benzamide in the form of a white solid (7 g), m.p. 122°-123° C.