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

HRID 358472

反応式

HRID 358472 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-d7cc5060a35a465399a53624fafdc06a
出典データセット
uspto-grants-1984_08
特許番号
US04468399

関連ノート

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