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2,4-Dichloroaniline → Isopropyl {4-chloro-2-[(2,4-dichlorophenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl}acetate

HRID 1398748
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HRID 1398748 반응식
Cl[C:2]1[N:6]([CH2:7][C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[C:5]2[C:14]([CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][CH:16]=[C:17]([Cl:18])[C:4]=2[N:3]=1.[Cl:24][C:25]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:26]=1[NH2:27].C(=O)([O-])O.[Na+]>CN1CCCC1=O>[Cl:18][C:17]1[C:4]2[N:3]=[C:2]([NH:27][C:26]3[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:25]=3[Cl:24])[N:6]([CH2:7][C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[C:5]=2[C:14]([CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][CH:16]=1
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HCID 111232,4-DichloroanilineHCID 516892Sodium BicarbonateHCID 86632857Isopropyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate

생성물 1

HCID 86632862Isopropyl {4-chloro-2-[(2,4-dichlorophenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl}acetate수율 21%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone
용매

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온도
100 °C

실험 절차

A mixture of isopropyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate (Reference Example 10; 1.96 g, 5.49 mmol), 2,4-dichloroaniline (2.67 g, 16.5 mmol) and N-methyl-2-pyrrolidinone (1.5 mL) was stirred at 100° C. for 15 hr. After cooling, the reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 3-15% ethyl acetate/n-hexane gradient mixture to give the title compound (546 mg, 1.13 mmol, 21%) as an oil.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a 3-15% ethyl acetate/n-hexane gradient mixture

출처 및 근거

ORD 기록
ord-83932af047214d9292adfca538fc840d
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901141B2

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