Triethylamine → (+/-)-1-Acetyl-4-acetylthio-2-pyrrolidone

HRID 2396875

Reaction equation

HRID 2396875 reaction equation
[C:1]([N:4]1[CH2:8][C@H:7]([C:9](=[O:11])[CH3:10])[CH2:6][C:5]1=[S:12])(=[O:3])[CH3:2].C(N(CC)CC)C.S1C=CC=C1CC(O)=O>C(OCC)(=O)C>[C:1]([N:4]1[CH2:8][CH:7]([C:9](=[O:11])[CH3:10])[CH2:6][C:5]1=[S:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 159702-Thiopheneacetic acidHCID 86748734(+)-(4R)-1-Acetyl-4-acetylthio-2-pyrrolidone

Product 1

HCID 86748735(+/-)-1-Acetyl-4-acetylthio-2-pyrrolidoneYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(+)-(4R)-1-Acetyl-4-acetylthio-2-pyrrolidone (3 g) and triethylamine (2.1 ml) are dissolved in ethyl acetate (30 ml), and the mixture is refluxed for three hours, and then allowed to stand at room temperature for 8 hours. To the reaction solution is added thiolacetic acid (1.2 ml), and the mixture is stirred at room temperature for 5 hours. The reaction solution is washed with water, dried, and evaporated to remove the solvent to give (±)-1-acetyl-4-acetylthio-2-pyrrolidone (2.7 g).

Workup

  1. temperaturethe mixture is refluxed for three hours
  2. washThe reaction solution is washed with water
  3. customdried
  4. customevaporated
  5. customto remove the solvent

Sources & evidence

ORD record
ord-17cfaadae93148f383e4d5451cdfd6d7
Source dataset
uspto-grants-1996_02
Patent number
US05495012

Linked notes

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