S(Cl)([Cl:3])=O.[CH2:5]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([S:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=O)=[CH:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:5]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([S:21][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:13]1[Cl:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1A solution of thionyl chloride (0.03 ml, 0.054 g, 0.45 mmol) in dry dichloromethane (5 ml) was added dropwise to a stirred solution of 1-benzyl-3-phenylsulfinylindole (0.150 g, 0.45 mmol) in dry dichloromethane (20 ml), containing suspended sodium bicarbonate (1 g), maintained at 0° C. One half hour after the addition was completed the reaction was quenched with a saturated solution of aqueous sodium bicarbonate. The organic phase was separated, combined with a dichloromethane extract of the aqueous phase and the combined organic phases were dried and evaporated in vacuo. Crystallization of the residue from dichloromethane/hexane gave the title product.
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