Dimethylacetamide → Ethyl 2-methoxyimino-2-(2-oxo-2,3-dihydro-1,3-thiazol-4-yl)acetate

HRID 2351203Notes

Reaction equation

HRID 2351203 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10]([CH2:12]Br)=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:14](=[S:19])([O:16]CC)[NH2:15].CC(N(C)C)=O>C(OCC)(=O)C>[CH3:1][O:2][N:3]=[C:4]([C:10]1[NH:15][C:14](=[O:16])[S:19][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 3032339O-Ethyl carbamothioateHCID 54053279Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-, ethyl ester

Product 1

HCID 54541877Ethyl 2-methoxyimino-2-(2-oxo-2,3-dihydro-1,3-thiazol-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 2-methoxyimino-4-bromoacetoacetate (a mixture of syn and anti isomers) (7.6 g.), O-ethyl thiocarbamate (3.0 g.) and dimethylacetamide (5 ml.) was stirred for 3 hours at 50° C. Ethyl acetate (50 ml.) was added to the reaction mixture and the resulting mixture was washed with water and with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. Ethyl acetate was distilled off to give crystalline residue. The residue was washed with diisopropyl ether to give ethyl 2-methoxyimino-2-(2-oxo-2,3-dihydro-1,3-thiazol-4-yl)acetate (syn isomer) (2.35 g.).

Workup

  1. washthe resulting mixture was washed with water and with a saturated sodium chloride aqueous solution
  2. dry with materialdried over magnesium sulfate
  3. distillationEthyl acetate was distilled off
  4. customto give crystalline residue
  5. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-013c38354a144512a8df3de8c5fbf52c
Source dataset
uspto-grants-1989_10
Patent number
US04871860

Reaction notes

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