Water → Ethyl 4,6-dichloro-3-formyl-1-[(4-methylphenyl)sulfonyl]-1H-indole-2-carboxylate

HRID 864522Notes

Reaction equation

HRID 864522 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([Cl:13])=[CH:9][C:10]=2[Cl:12])[NH:5][C:4]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:2].C(=O)([O-])[O-].[K+].[K+].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.O>CN(C)C=O>[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([Cl:13])=[CH:9][C:10]=2[Cl:12])[N:5]([S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:33])=[O:32])[C:4]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 2794948ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylate

Product 1

HCID 11305239Ethyl 4,6-dichloro-3-formyl-1-[(4-methylphenyl)sulfonyl]-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 3-formyl-2-carboethoxy-4,6-dichloroindole (46.3 g. 162 mmol) and anhydrous potassium carbonate (44.9 g, 325 mmol) in dimethylformamide (600 mL). Add p-toluenesulfonyl chloride (42.9 g, 225 mmol). After 18 hours, pour the reaction mixture into water (3 L) and stir to give a solid. Filter, rinse with water and diethyl ether, and recrystallize from acetonitrile/dichloroethane to give the title compound.

Workup

  1. customto give a solid
  2. filtrationFilter
  3. washrinse with water and diethyl ether
  4. customrecrystallize from acetonitrile/dichloroethane

Sources & evidence

ORD record
ord-be2b6ae2621a42f7b79302b9a94e1c33
Source dataset
uspto-grants-1996_10
Patent number
US05563157

Reaction notes

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