Sodium Acetate → HCID 54434053, compound

HRID 1649404Notes

Reaction equation

HRID 1649404 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5](=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6](=O)[CH2:7]Cl)[CH3:2].[NH2:18][C:19]([NH2:21])=[S:20].C([O-])(=O)C.[Na+]>O1CCCC1.O>[CH2:1]([O:3][C:4](=[O:17])[C:5]([C:6]1[N:18]=[C:19]([NH2:21])[S:20][CH:7]=1)=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 53900417HCID 53900417, compound

Product 1

HCID 54434053HCID 54434053, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

209.2 g of 2-benzylidene-3-oxo-4-chlorobutyric acid ethyl ester (described in J. Amer. Chem. Soc. 66, 1933 (1944)), 63.2 g of thiourea and 104.6 g of sodium acetate were dissolved in a mixture of 1,460 ml of tetrahydrofuran and 630 ml of water. The solution was stirred overnight at room temperature and the tetrahydrofuran was then evaporated off. The aqueous phase was adjusted to pH 8 and extracted three times with ethyl acetate. Drying and evaporation of the organic phase gave a viscous oil, which chiefly consisted of the desired Z-isomer. The product was further processed in the crude form.

Workup

  1. customthe tetrahydrofuran was then evaporated off
  2. extractionextracted three times with ethyl acetate
  3. customDrying
  4. customevaporation of the organic phase
  5. customgave a viscous oil, which

Sources & evidence

ORD record
ord-fd0a23a80efc4267b2d1cfa57032c529
Source dataset
uspto-grants-1983_11
Patent number
US04416880

Reaction notes

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