Thioacetamide → HCID 53983477, compound

HRID 2352728Notes

Reaction equation

HRID 2352728 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].[CH3:5][O:6][N:7]=[C:8]([C:14]([CH2:16]Br)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(O)C>[CH3:5][O:6][N:7]=[C:8]([C:14]1[N:4]=[C:1]([CH3:2])[S:3][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 54053279Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-, ethyl ester

Product 1

HCID 53983477HCID 53983477, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Thioacetamide (3.8 g.) was added to a solution of ethyl 2-methoxyimino-4-bromoacetoacetate (a mixture of syn and anti isomers) (12.6 g.) in ethanol (50 ml.) and the mixture was stirred for 5 hours at 50° C. Ethanol was distilled off under reduced pressure and water was added to the residue. The resulting mixture was extracted with ethyl acetate. The extract was in turn washed with water, a sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give ethyl 2-methoxyimino-2-(2-methyl-1,3-thiazol-4-yl)acetate (a mixture of syn and anti isomers) (9.0 g.).

Workup

  1. distillationEthanol was distilled off under reduced pressure and water
  2. additionwas added to the residue
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materiala sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-91483e126b524892889dde6621a5d0ff
Source dataset
uspto-grants-1989_10
Patent number
US04877873

Reaction notes

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