Potassium Carbonate → HCID 53744366, compound

HRID 745596Notes

Reaction equation

HRID 745596 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[C:20]([S:23][CH2:24][CH:25]([CH3:29])[C:26](Cl)=[O:27])(=[O:22])[CH3:21]>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[C:26](=[O:27])[CH:25]([CH3:29])[CH2:24][S:23][C:20](=[O:22])[CH3:21])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 2794655Methyl indoline-2-carboxylate

Product 1

HCID 53744366HCID 53744366, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To the stirred mixture of 5.0 g of indoline-2-carboxylic acid methyl ester [J. Am. Chem. Soc. 92, 2476 (1970)], 7.8 g of powdered potassium carbonate and 50 ml of methylene chloride, 5.1 g of 3-acetylthio-2-methylpropanoyl chloride (Belgium Pat. No. 868,532) in 20 ml of methylene chloride are added during 3 minutes at room temperature. After 2 hours the mixture is diluted with 100 ml of methylene chloride and washed with 100 ml of water, 100 ml of 1N hydrochloric acid and 100 ml of saturated aqueous sodium bicarbonate. The organic layer is dried and evaporated, to give the 1-(3-acetylthio-2-methylpropanoyl)-indoline-2-carboxylic acid methyl ester as an oil, showing in the IR-spectrum bands at 1710, 1690 and 1675 cm-1.

Workup

  1. washwashed with 100 ml of water, 100 ml of 1N hydrochloric acid and 100 ml of saturated aqueous sodium bicarbonate
  2. customThe organic layer is dried
  3. customevaporated

Sources & evidence

ORD record
ord-9b19968f52534adf8c552e56b161782d
Source dataset
uspto-grants-1986_07
Patent number
US04599357

Reaction notes

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