Thioacetamide → HCID 53983477, compound

HRID 1382108Notes

Reaction equation

HRID 1382108 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-8996fd23e8f646f993e92095eb8fe001
Source dataset
uspto-grants-1989_02
Patent number
US04804752

Reaction notes

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