Thioacetamide → HCID 11777439, compound

HRID 1735826Notes

Reaction equation

HRID 1735826 reaction equation
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:17]([NH2:20])(=[S:19])[CH3:18]>C(O)C>[CH3:18][C:17]1[S:19][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:20]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 10085313HCID 10085313, compound

Product 1

HCID 11777439HCID 11777439, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.4 g of ethyl 2-bromo-3-(4-methylphenyl)-3-oxopropanoate in 30 ml of anhydrous ethanol is added with 1.4 g of thioacetamide and the mixture is refluxed for 4 hours. The solvent is evaporated and the residue is dissolved in H2O and alkalinized to pH 10 with 10% NaOH, extracted 2 times with ether and the organic phase is washed with brine, dried and evaporated to dryness under reduced pressure. The residue is purified by F.C. (eluent 90:10 hexane:ethyl acetate) and 1.65 g of a light yellow solid are obtained (41% yield). 1H NMR (CDCl3), δ: 1.28 (t, 3 H), 2.39 (s, 3 H), 2.73 (s, 3 H), 4.26 (q, 2 H), 7.23 (d, 2 H), 7.62 (d, 2 H).

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. customThe solvent is evaporated
  3. dissolutionthe residue is dissolved in H2O
  4. extractionextracted 2 times with ether
  5. washthe organic phase is washed with brine
  6. customdried
  7. customevaporated to dryness under reduced pressure
  8. customThe residue is purified by F.C

Sources & evidence

ORD record
ord-2daffee9316f4af98bac39a02075562a
Source dataset
uspto-grants-1996_07
Patent number
US05538987

Reaction notes

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