Ethanol → Ethyl 2-(diethoxymethyl)thiazole-4-carboxylate

HRID 907379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907379
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C:5](=[S:7])[NH2:6])[CH3:2].C([CH:13](Br)[C:14](=O)[C:15]([O-:17])=[O:16])C.[CH2:20](O)[CH3:21]>>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C:5]1[S:7][CH:13]=[C:14]([C:15]([O:17][CH2:20][CH3:21])=[O:16])[N:6]=1)[CH3:2]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 27947342,2-DiethoxythioacetamideHCID 21948992Ethylbromopyruvate

Produkt 1

HCID 16220290Ethyl 2-(diethoxymethyl)thiazole-4-carboxylateAusbeute 93 %

Versuchsvorschrift

2,2-Diethoxyethanethioamide (0.654 g, 6.03 mmol; see step (iii) above) and ethylbromopyruvate (Aldrich) (1.28 g, 6.10 mmol) were dissolved in ethanol (10 mL) in the presence of 4 Å molecular sieves (1 g). The mixture was refluxed for 45 min and the solvent removed under reduced pressure. The residue was then dissolved in ethyl acetate (20 mL) and extracted with saturated. NaHCO3 solution (2×20 mL), and brine (2×20 mL). The organic fraction was then dried (MgSO4), filtered and the solvent removed under reduced pressure to yield the sub-title compound (1.452 g, 93%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 45 min
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue was then dissolved in ethyl acetate (20 mL)
  4. extractionextracted with saturated
  5. dry with materialThe organic fraction was then dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cdb771d46e084b72ae9df8d9524a6f1a
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012967B2

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