Ethanol → Ethyl 2-((dimethylamino)methyl)thiazole-4-carboxylate

HRID 358472

Reaktionsgleichung

Reaktionsgleichung von HRID 358472
Cl.[CH3:2][N:3]([CH2:5][C:6]([NH2:8])=[S:7])[CH3:4].Br[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(O)C>CCOCC.O>[CH3:2][N:3]([CH2:5][C:6]1[S:7][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:8]=1)[CH3:4]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 66144Ethyl bromopyruvateHCID 13121932N,N-Dimethylaminothioacetamide hydrochloride

Produkt 1

HCID 2039211Ethyl 2-((dimethylamino)methyl)thiazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A reaction mixture was prepared containing 15.5 g. of dimethylaminothioacetamide hydrochloride, 20.5 g. of ethyl bromopyruvate and 100 ml. of ethanol. The reaction mixture was heated to refluxing temperature for about four hours after which time the solvent was removed in vacuo in a rotary evaporator. The residue, containing ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate formed in the above reaction, was dissolved in a mixture of ether and water. The aqueous layer was separated. The ether layer was extracted with an equal volume of water and then discarded. The two aqueous layers were combined and washed with ether. The ether layer was again discarded and the aqueous layer cooled to a temperature in the range of 0°-5° C. Solid potassium carbonate was added until the aqueous layer gave a basic reaction to litmus. An oil separated comprising ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate free base. The oily layer was extracted with ether and the ether extract separated and dried. The ether was removed by evaporation in vacuo. The resulting residue was purified by gradient high pressure liquid chromatography (silica ethyl acetate). Ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate thus obtained had the following physical characteristics:

Aufarbeitung

  1. customA reaction mixture was prepared
  2. additioncontaining 15.5 g
  3. temperatureThe reaction mixture was heated
  4. temperatureto refluxing temperature for about four hours after which time the solvent
  5. customwas removed in vacuo in a rotary evaporator
  6. additionThe residue, containing ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate
  7. customformed in the above reaction
  8. customThe aqueous layer was separated
  9. extractionThe ether layer was extracted with an equal volume of water
  10. washwashed with ether
  11. temperaturethe aqueous layer cooled to a temperature in the range of 0°-5° C
  12. additionSolid potassium carbonate was added until the aqueous layer
  13. customgave
  14. customa basic reaction to litmus
  15. customAn oil separated
  16. extractionThe oily layer was extracted with ether
  17. extractionthe ether extract
  18. customseparated
  19. customdried
  20. customThe ether was removed by evaporation in vacuo
  21. customThe resulting residue was purified by gradient high pressure liquid chromatography (silica ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d7cc5060a35a465399a53624fafdc06a
Quelldatensatz
uspto-grants-1984_08
Patentnummer
US04468399

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