Indole → 1-(Phenylsulfonyl)-1H-indole

HRID 1798016Notes

Reaction equation

HRID 1798016 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]1([S:16](Cl)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.C(Cl)Cl>[C:10]1([S:16]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 798IndoleHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 3150171-(Phenylsulfonyl)-1H-indoleYield 89%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(phenylsulphonyl)indole is prepared according to the procedures described in S. Roy, G. W. Gribble Tetrahedron Lett. 2005, 46, 1325-1328, by reaction of indole with phenylsulphonyl chloride (PhSO2C1) in a basic medium (NaOH) in the presence of a catalytic quantity of (n-Bu)4NHSO4 in CH2Cl2 at 0° C. for 1 hour then at ambient temperature for 4 hours (yield: 89%).

Sources & evidence

ORD record
ord-400a3cbe7a8a4401b87b716ba19f9a70
Source dataset
uspto-grants-2013_01
Patent number
US08343964B2

Reaction notes

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