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

HRID 21737

Reaction equation

HRID 21737 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-78b65f57d4cc4543959bfb9496b3572a
Source dataset
uspto-grants-1995_06
Patent number
US05424446

Linked notes

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