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

HRID 1089969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1089969
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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.).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-863260a43d18425fb977cde5bcd2f720
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05079369

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