Chlorosulfonic acid → 1-Acetyl-2,3-dihydro-1H-indole-5-sulfonyl chloride

HRID 1081343Notes

Reaction equation

HRID 1081343 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl:13][S:14](O)(=[O:16])=[O:15]>>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:14]([Cl:13])(=[O:16])=[O:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 276731-(2,3-Dihydro-1H-indol-1-yl)ethan-1-one

Product 1

HCID 140245961-Acetyl-2,3-dihydro-1H-indole-5-sulfonyl chloride

Conditions

Temperature
60 °C

Procedure

A 1.02 g portion of 1-acetylindoline was treated with 2 mL of chlorosulfonic acid at 0° C. The mixture was heated at 60° C. for 2 h, then treated with crushed ice, filtered and dried to give 1.3 g of the title compound which was used directly for subsequent reaction. TLC: Rf=0.18, 50% EtOAc/hexane. (1H)-NMR (CDCl3) consistent with structure.

Workup

  1. additiontreated with crushed ice
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-fb971f55ae6f4fa99ec12f3d481213da
Source dataset
uspto-grants-1996_12
Patent number
US05585397

Reaction notes

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