4-Nitrobenzenesulfonyl chloride → HCID 8194946, compound

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14]1([CH3:26])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:23]2[CH2:24][CH2:25][N:20]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH3:26])[CH2:21][CH2:22]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Procedure

A mixture of 7.88 g (0.0356 m) of p-nitrobenzenesulfonylchloride, 6.27 g (0.0356 m) of 1-(o-tolyl)piperazine, 4.96 ml (0.0356 m) of triethylamine, and 100 ml of tetrahydrofuran is stirred at room temperature for 18 hours. The solvent is then removed in vacuo and the residue is extracted with methylene chloride/aqueous sodium bicarbonate and brine. The organic layer is filtered through sodium sulfate and taken to dryness. Crystallization from methylene chloride/Skellysolve® B hexanes gives 9.51 g of 1-[(p-nitrophenyl)sulfonyl]-4-(o-methylphenyl)piperazine of melting point 176°-177.5° C. and 1.33 g of a second crop (84%).