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Ethyl chloroacetate → Ethyl [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetate

HRID 660854
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HRID 660854 반응식
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([CH:20]3[CH2:22][CH2:21]3)[C:16](=[O:19])[NH:17][N:18]=2)=[CH:10][CH:9]=1.Cl[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(#N)C>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][N:17]1[C:16](=[O:19])[N:15]([CH:20]2[CH2:22][CH2:21]2)[C:14]([C:11]2[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=2)=[N:18]1)[CH3:29]
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참가 물질

5

반응물 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 580121993-(4-Chlorophenyl)-4-cyclopropyl-1H-1,2,4-triazol-5(4H)-one

생성물 1

HCID 58011757Ethyl [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

586 mg (4.24 mmol) of potassium carbonate are added to 500 mg (2.12 mmol) of 5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one from Example 36A and 260 mg (2.12 mmol) of ethyl chloroacetate in 10 ml acetonitrile and the mixture is heated under reflux with stirring for 2 hours. It is then concentrated, the residue taken up in water is extracted with dichloromethane, the organic phase dried over sodium sulphate and again concentrated. After purification by flash chromatography over silica gel (eluent: first dichloromethane, then dichloromethane/methanol 100:1) 448 mg (66% of theory) of the target compound are obtained.

후처리

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. concentrationIt is then concentrated
  4. extractionis extracted with dichloromethane
  5. dry with materialthe organic phase dried over sodium sulphate
  6. concentrationagain concentrated
  7. customAfter purification by flash chromatography over silica gel (eluent
  8. customfirst dichloromethane, then dichloromethane/methanol 100:1) 448 mg (66% of theory) of the target compound are obtained

출처 및 근거

ORD 기록
ord-2689912a8a144a7287cf86e2ee00e50c
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08084481B2

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