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Ethyl Acetate → 2-(3-Pyridyl)-4-(3-cyanophenyl)-5-carboethoxythiazole

HRID 1062672
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HRID 1062672 반응식
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=1)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:18]([NH2:26])(=[S:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1.C(OCC)(=O)C>O1CCCC1>[N:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:18]2[S:25][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=3)[N:26]=2)[CH:20]=1
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참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 737155ThionicotinamideHCID 22282470Ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate

생성물 1

HCID 222824922-(3-Pyridyl)-4-(3-cyanophenyl)-5-carboethoxythiazole수율 23%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

To a solution of ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate (1.0 g, 3.4 mmol) in 20 mL of tetrahydrofuran was added thionicotinamide (0.46 g, 3.4 mmol). The resulting mixture was stirred at 65° C. for 16 h. The reaction was allowed to cool and the solvent was evaporated in vacuo. The residue was triturated with chloroform, taken up in ethyl acetate, washed with saturated aq Na2CO3 and brine, dried (MgSO4) and concentrated in vacuo to yield a solid. Trituration with ethyl acetate left the title compound as an off-white solid (0.26 g, 23%). MS (ESI) 336.1 (M+H)+.

후처리

  1. temperatureto cool
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was triturated with chloroform
  4. washwashed with saturated aq Na2CO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto yield a solid

출처 및 근거

ORD 기록
ord-0749c6ecbf2a4083aea68fb0a614a07c
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06962935B2

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