Methanol → Ethyl 2-(pyridin-3-YL)thiazole-4-carboxylate

HRID 1174159노트

반응식

HRID 1174159 반응식
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14].CO>C(O)C.C(Cl)(Cl)Cl>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1]2[S:8][CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:9]=2)[CH:3]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 66144Ethyl bromopyruvateHCID 737155Thionicotinamide

생성물 1

HCID 2824169Ethyl 2-(pyridin-3-YL)thiazole-4-carboxylate수율 71.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6212Chloroform용매

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온도
70 °C

실험 절차

A solution containing thionicotinamide (30 g, 217.1 mmol) in ethanol (540 mL) was treated with ethyl bromopyruvate (30.3 mL, 241.4 mmol), heated at 70° C. for 3 hours, cooled to 25° C., concentrated and partitioned between chloroform and saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with chloroform and then with 15% methanol in chloroform containing 1% ammonium hydroxide to give the product (36.3 g, 71% yield).

후처리

  1. temperaturecooled to 25° C.
  2. concentrationconcentrated
  3. custompartitioned between chloroform and saturated NaHCO3
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting with chloroform

출처 및 근거

ORD 기록
ord-3795f0d265e94c1dab9454718bcff6e6
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834043B2

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