Sodium → HCID 86740890, compound

HRID 745603Notes

Reaction equation

HRID 745603 reaction equation
[Na].[C:2]([OH:5])(=[S:4])[CH3:3].[CH2:6]([O:8][C:9]([CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]1[C:20](=[O:24])[CH:21](Br)[CH3:22])=[O:10])[CH3:7]>C(O)C>[CH2:6]([O:8][C:9]([CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]1[C:20](=[O:24])[CH:21]([S:4][C:2](=[O:5])[CH3:3])[CH3:22])=[O:10])[CH3:7]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 53790423HCID 53790423, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86740890HCID 86740890, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 0.35 g of sodium in 50 ml of ethanol, 1.2 g of thioacetic acid are added and the mixture stirred for 0.5 hours at room temperature. Then 4.5 g 1-(2-bromopropanoyl)-indoline-2-carboxylic acid ethyl ester are added and the mixture is refluxed for 8 hours. It is cooled to room temperature, evaporated, and the residue partitioned between 30 ml of methylene chloride, 70 ml of diethyl ether and 50 ml of water. The organic layer is dried and evaporated, to yield the 1-(2-acetylthiopropanoyl)-indoline-2-carboxylic acid ethyl ester as an oil.

Workup

  1. temperaturethe mixture is refluxed for 8 hours
  2. temperatureIt is cooled to room temperature
  3. customevaporated
  4. customthe residue partitioned between 30 ml of methylene chloride, 70 ml of diethyl ether and 50 ml of water
  5. customThe organic layer is dried
  6. customevaporated

Sources & evidence

ORD record
ord-4a33676e261547c2abb5dfe0939e9ed4
Source dataset
uspto-grants-1986_07
Patent number
US04599357

Reaction notes

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