4-Toluenesulfonyl chloride → HCID 18703634, compound
Reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][N:13]1[CH:21]([CH2:22][CH2:23]O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:25]>C(Cl)Cl>[CH3:12][N:13]1[CH:21]([CH2:22][CH2:23][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:25]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
p-Toluene sulfonyl chloride (2.3 g, 12.1 mmol) is added to a solution of TEA (3.5 g, 34.5 mmol) and 1,3-dihydro-2-methyl-3-(2-hydroxyethyl)-2H-isoindol-1-one (2.2 g, 11.5 mmol) in 50 mL of CH2Cl2 at room temperature under argon. The mixture is stirred at room temperature overnight and washed with water (3×50 mL). The organic layer is dried over Na2SO4 and evaporated to give an oil which is chromatographed in ethyl acetate over silica gel to give 1.5 g (38% yield) of 1,3-dihydro-2-methyl-3-(2-tosylethyl)-2H-isoindol-1-one.