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

HRID 354602

Reaction equation

HRID 354602 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

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 over silica using a toluene-ethyl acetate eluant. Ethyl 2 -(dimethylaminomethyl)-4-thiazolecarboxylate thus obtained had the following physical characteristics:

Workup

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

Sources & evidence

ORD record
ord-0f4fd68553cc4f1b93cdd0e8ea6b275d
Source dataset
uspto-grants-1983_03
Patent number
US04375547

Linked notes

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