Chlorosulfonic acid → HCID 86692805, compound

HRID 1751972Notes

Reaction equation

HRID 1751972 reaction equation
SC1C=C2C(=CC=1)NC(=O)C2.[CH3:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH2:15][C:16](=[O:22])[NH:17]2.[Cl:23][S:24](O)(=[O:26])=[O:25]>>[Cl:23][S:24]([C:21]1[C:13]([CH3:12])=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:22])[CH2:15]2)(=[O:26])=[O:25]

Participants

4

Reactant 3

HCID 24638Chlorosulfonic acidHCID 11983903794521-56-5HCID 125793824-Methyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 86692805HCID 86692805, compound

Procedure

Under reaction conditions analogous to preparation of 5-mercaptooxindole, chlorosulfonylation of 4-methyloxindole 3.15 g (21.40 mmol) with neat chlorosulfonic acid 25 mL provided 4.55 g of 5-chlorosulfonyl-4-methyloxindole (86.5% Y, 95% isomeric purity by 1H-NMR, in d6-acetone) which was reduced with triphenyl phosphine 17.0 g (65 mmol) in anhydrous dichloromethane, to provide a crude thiol 2.573 g (75% Y) which was then methylated with excess of methyl iodide (1.50 mL; 24 mmol) to provide a crude methylthio intermediate 2.722 g (98% Y, 90% pure), by using conditions analogous to preparation of 5-methylsulfoxyoxindole.

Workup

  1. customUnder reaction conditions

Sources & evidence

ORD record
ord-68f68ac99132413a9ee2d5fb0bf3229d
Source dataset
uspto-grants-2015_10
Patent number
US09162981B2

Reaction notes

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