Acetic Anhydride → 1-(1-Benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-ethanone

HRID 1403973Notes

Reaction equation

HRID 1403973 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C(O[C:9](=[O:11])[CH3:10])(=O)C.[C:12]1([S:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[C:12]1([S:18]([N:21]2[C:29]3[C:24](=[CH:25][C:26]([C:9](=[O:11])[CH3:10])=[CH:27][CH:28]=3)[CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 6687571-(benzenesulfonyl)-2,3-dihydroindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 141129561-(1-Benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of AlCl3 (144 g, 1.08 mol) in CH2Cl2 (1070 mL) was added acetic anhydride (54 mL). The mixture was stirred for 15 minutes before a solution of 1-(phenylsulfonyl)indoline (46.9 g, 0.180 mol) in CH2Cl2 (1070 mL) was added dropwise. The mixture was stirred for 5 h and was quenched by the slow addition of crushed ice. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organics were washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated under vacuum to obtain 1-(1-(phenylsulfonyl)indolin-5-yl)ethanone (42.6 g).

Workup

  1. additionwas added dropwise
  2. customwas quenched by the slow addition of crushed ice
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. washThe combined organics were washed with saturated aqueous NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-553b617f21aa423aab2759cd8d679584
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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