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

HRID 1628392노트

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HRID 1628392 반응식
Cl[C:2]1[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2[C:13]([CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][CH:15]=[C:16]([Cl:17])[C:4]=2[N:3]=1.[Cl:23][C:24]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:25]=1[NH2:26].C(=O)([O-])O.[Na+]>CN1CCCC1=O>[Cl:17][C:16]1[C:4]2[N:3]=[C:2]([NH:26][C:25]3[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:24]=3[Cl:23])[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]=2[C:13]([CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 111232,4-DichloroanilineHCID 516892Sodium BicarbonateHCID 86632860Ethyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate

생성물 1

HCID 86632861Ethyl [4-chloro-2-[(2,4-dichlorophenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate수율 12%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
100 °C

실험 절차

A mixture of ethyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate (708 mg, 2.06 mmol), 2,4-dichloroaniline (1.00 g, 6.19 mmol) and N-methyl-2-pyrrolidinone (0.5 mL) was stirred at 100° C. for 3.5 days. After cooling, the reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by basic silica gel column chromatography eluting with a 3-15% ethyl acetate/n-hexane gradient mixture. The resulting solid was washed with n-hexane to give the title compound (115 mg, 0.245 mmol, 12%) as a colorless solid.

후처리

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

출처 및 근거

ORD 기록
ord-e3338e2d75a946df8a0703ab8302e290
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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