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Ethyl chloroacetate → Ethyl [4-(5-chloro-2-thienyl)-3-(2-fluorobenzyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

HRID 660909
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HRID 660909 반응식
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:10](=[O:20])[NH:9][CH:8]=2)=[CH:4][CH:3]=1.Cl[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][N:9]1[CH:8]=[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:10]1=[O:20])[CH3:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 580122955-(5-chloro-2-thienyl)-1-(2-fluorobenzyl)-1,3-dihydro-2H-imidazol-2-one

생성물 1

HCID 58012258Ethyl [4-(5-chloro-2-thienyl)-3-(2-fluorobenzyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetate

시약·촉매·용매 2

HCID 6342Acetonitrile용매
HCID 8857
Ethyl Acetate
용매

실험 절차

650 mg (2.15 mmol) of 5-(5-chloro-2-thienyl)-1-(2-fluorobenzyl)-1,3-dihydro-2H-imidazol-2-one from Example 236A, 516 mg (4.21 mmol) of ethyl chloroacetate and 582 mg (4.21 mmol) of potassium carbonate are stirred in 12 ml acetonitrile for 7 hrs at 80° C. The reaction solution is diluted with ethyl acetate and washed three times with saturated sodium chloride solution. The organic phase is dried over sodium sulphate. After filtration from the drying agent, the filtrate is concentrated in vacuo. After purification by flash chromatography over silica gel (eluent: cyclohexane/ethyl acetate first 5:1, then 1:1), 610 mg (74% of theory) of the target compound are obtained.

후처리

  1. washwashed three times with saturated sodium chloride solution
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationAfter filtration from the drying agent
  4. concentrationthe filtrate is concentrated in vacuo
  5. customAfter purification by flash chromatography over silica gel (eluent
  6. customcyclohexane/ethyl acetate first 5:1, then 1:1), 610 mg (74% of theory) of the target compound are obtained

출처 및 근거

ORD 기록
ord-f0c2124665ae45cc9ce4b67f4bccbb7a
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08084481B2

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