Thioacetamide → HCID 53983477, compound

HRID 463862Notes

Reaction equation

HRID 463862 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-86a64bfba8d1471abdf140425b9a6d0c
Source dataset
uspto-grants-1985_10
Patent number
US04544653

Reaction notes

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