Benzenesulfonyl chloride → 1-(benzenesulfonyl)-2,3-dihydroindole

HRID 2404670Notes

Reaction equation

HRID 2404670 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]1([S:7]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 10328Indoline

Product 1

HCID 6687571-(benzenesulfonyl)-2,3-dihydroindoleYield 96.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of DMAP (1.5 g), benzenesulfonyl chloride (24 g, 136 mmol) and 2,3-dihydro-1H-indole (14.7 g, 124 mmol) in CH2Cl2 (200 mL) was added dropwise Et3N (19 g, 186 mmol) in an ice-water bath. After addition, the mixture was stirred at room temperature overnight, washed with water, dried over Na2SO4 and concentrated to dryness under reduced pressure to provide 1-benzenesulfonyl-2,3-dihydro-1H-indole (30.9 g, 96%).

Workup

  1. additionAfter addition
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-197289e9ca414bd49d3aa63228545dea
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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