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Ethyl bromopyruvate → Ethyl 2-cyclopropylthiazole-4-carboxylate

HRID 1654210
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HRID 1654210 반응식
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:10]1([C:13](=[S:15])[NH2:14])[CH2:12][CH2:11]1>C(O)C>[CH:10]1([C:13]2[S:15][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:14]=2)[CH2:12][CH2:11]1
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참가 물질

4

반응물 2

HCID 66144Ethyl bromopyruvateHCID 22140884Cyclopropanecarbothioamide

생성물 1

HCID 18771956Ethyl 2-cyclopropylthiazole-4-carboxylate수율 23.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of ethyl bromopyruvate (3.6 g), cyclopropanethioamide (2.2 g) and ethanol (30 ml) was refluxed for two hours. The reaction mixture was cooled, then ethanol was distilled off under reduced pressure. To the residue was added water (30 ml), which was subjected to extraction with ethyl acetate (50 ml) twice. The extract solution was washed with water (30 ml), followed by drying over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel chromatography (2.5×30 cm), eluting with ethyl acetate-hexane (1:3). The desired fraction was concentrated to give ethyl 2-cyclopropyl-4-thiazolcarboxylate (0.84 g) as pale yellow needles.

후처리

  1. temperaturewas refluxed for two hours
  2. temperatureThe reaction mixture was cooled
  3. distillationethanol was distilled off under reduced pressure
  4. additionTo the residue was added water (30 ml), which
  5. extractionwas subjected to extraction with ethyl acetate (50 ml) twice
  6. washThe extract solution was washed with water (30 ml)
  7. dry with materialby drying over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. washeluting with ethyl acetate-hexane (1:3)
  10. concentrationThe desired fraction was concentrated

출처 및 근거

ORD 기록
ord-c8d0e8c668f646c48596e78cfea83cb6
출처 데이터셋
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05405861

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