Acetic Anhydride → N-acetyl-2-furfurylthioacetamide

HRID 52436Notes

Reaction equation

HRID 52436 reaction equation
[CH2:1]([CH2:7][C:8]([NH2:10])=[S:9])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12].C(OCC)(=O)C>N1C=CC=CC=1>[C:11]([NH:10][C:8](=[S:9])[CH2:7][CH2:1][C:2]1[O:6][CH:5]=[CH:4][CH:3]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 199636792-Furfurylthioacetamide

Product 1

HCID 19963689N-acetyl-2-furfurylthioacetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

8.56 g (0.05 mol) of 2-furfurylthioacetamide, 5.61 g (0.055 mol) of acetic anhydride, and 6.11 g (0.05 mol) of N,N-dimethyl-aminopyridine were dissolved in 50 ml of pyridine. The mixture was stirred at 80° C. for 16 hours. The solvent was distilled away from the reaction mixture, and the residue thus obtained was added to ethyl acetate and washed successively with water, 1N hydrochloric acid, water three times, and brine. A resultant organic extract layer was dried, and the solvent was distilled away therefrom, so that N-acetyl-2-furfurylthioacetamide was obtained in a yield of 7.11 g (60%).

Workup

  1. distillationThe solvent was distilled away from the reaction mixture
  2. customthe residue thus obtained
  3. washwashed successively with water, 1N hydrochloric acid, water three times, and brine
  4. customA resultant organic extract layer was dried
  5. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-76330c2324714914941aad18f42a0b71
Source dataset
uspto-grants-1997_04
Patent number
US05616711

Reaction notes

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