4-Methoxybenzenesulfonyl chloride → HCID 22642542, compound

HRID 1532999Notes

Reaction equation

HRID 1532999 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-e5b871703a154be294aece2cdc4b633d
Source dataset
uspto-grants-2001_03
Patent number
US06207672B1

Reaction notes

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