Potassium Carbonate → HCID 53850110, compound

HRID 745599Notes

Reaction equation

HRID 745599 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15][CH3:16])[CH:12]=2)[NH:7]1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:23]([S:26][CH2:27][CH:28]([CH3:32])[C:29](Cl)=[O:30])(=[O:25])[CH3:24]>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15][CH3:16])[CH:12]=2)[N:7]1[C:29](=[O:30])[CH:28]([CH3:32])[CH2:27][S:26][C:23](=[O:25])[CH3:24])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 128420382,3-Dihydro-5-methoxy-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 53850110HCID 53850110, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the stirred mixture of 4.0 g of 5-methoxyindoline-2-carboxylic acid ethyl ester, 5.0 g of powdered potassium carbonate and 50 ml of methylene chloride, 3.3 g of 3-acetylthio-2-methylpropanoyl chloride in 10 ml of methylene chloride are added during 1 minute. After stirring for 2 hours at reflux the mixture is cooled to room temperature and partitioned between 50 ml of water and 100 ml of diethyl ether. The organic layer is washed with 50 ml of water, 50 ml of 1N hydrochloric acid and 50 ml of saturated aqueous sodium chloride, dried and evaporated, to give the 1-(3-acetylthio-2-methylpropanoyl)-5-methoxyindoline-2-carboxylic acid ethyl ester as an oil.

Workup

  1. additionare added during 1 minute
  2. temperatureat reflux the mixture
  3. custompartitioned between 50 ml of water and 100 ml of diethyl ether
  4. washThe organic layer is washed with 50 ml of water, 50 ml of 1N hydrochloric acid and 50 ml of saturated aqueous sodium chloride
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-4fc9ea5a892e49ef8fcb8568f8726c9e
Source dataset
uspto-grants-1986_07
Patent number
US04599357

Reaction notes

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