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

HRID 1915271Notes

Reaction equation

HRID 1915271 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)-ethanoneYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring 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. A solution of 1-benzenesulfonyl-2,3-dihydro-1H-indole (46.9 g, 0.18 mol) in CH2Cl2 (1070 mL) was added dropwise. The mixture was stirred for 5 h and quenched by the slow addition of crushed ice. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated under vacuum to yield 1-(1-benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-ethanone (42.6 g, 79%).

Workup

  1. stirringThe mixture was stirred for 5 h
  2. customquenched by the slow addition of crushed ice
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. washThe combined organic layers were washed with saturated aqueous NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2e1a8d0356a943b19d2da2a4aa0a98a1
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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