4-Methoxybenzenesulfonyl chloride → HCID 22642542, compound

HRID 2414724Notes

Reaction equation

HRID 2414724 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=[O:11].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>C(=O)([O-])[O-].[Na+].[Na+]>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH:2]2[C:10]([OH:12])=[O:11])(=[O:23])=[O:22])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 86074Indoline-2-carboxylic acid

Product 1

HCID 22642542HCID 22642542, compound

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

At 50° C. and 0.02 mbar, 1 g (6.1 mmol) of indoline-2-carboxylic acid and 2.5 g (12.2 mmol) of 4-methoxybenzenesulfonyl chloride are kept for 4 hours (h) in a kugelrohr which is rotated slowly and continuously. The brown crystalline product is subsequently taken up in sodium carbonate solution and extracted twice with diethyl ether. The aqueous phase is acidified using 6 N HCl and extracted four times with ethyl acetate. The combined organic phases are extracted with saturated NaCl solution, dried over sodium sulfate and concentrated under reduced pressure. Residual solvent is removed using oil pump vacuum.

Workup

  1. extractionextracted twice with diethyl ether
  2. extractionextracted four times with ethyl acetate
  3. extractionThe combined organic phases are extracted with saturated NaCl solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customResidual solvent is removed

Sources & evidence

ORD record
ord-4ab1f958a8ae482c83d3c1249b896231
Source dataset
uspto-grants-2004_11
Patent number
US06815440B2

Reaction notes

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