Azobisisobutyronitrile → Ethyl 4-[4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]butanoate

HRID 1398758노트

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HRID 1398758 반응식
[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13](=[O:15])[NH:14][C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].N(C(C)(C)C#N)=NC(C)(C)C#N.[Cl:36]N1C(=O)CCC1=O>ClC1C=CC=CC=1>[Cl:36][C:9]1[C:10]2[NH:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11]=2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 31398ChlorosuccinimideHCID 68760821HCID 68760821, 화합물

생성물 1

HCID 68773903Ethyl 4-[4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]butanoate수율 63.2%

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

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온도
85 °C

실험 절차

To a solution of ethyl 4-[7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]butanoate (9.7 g, 30.5 mmol) and 2,2′-azobisisobutyronitrile (AIBN; 0.5 g, 3.05 mmol) in chlorobenzene (100 mL) was added N-chlorosuccinimide (NCS; 4.35 g, 32.6 mmol) in portions at 65° C., and the mixture was stirred at 80-90° C. for 2 days. After cooled to room temperature, the reaction mixture was partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous phase was extracted with ethyl acetate (100 ml×3), washed with brine (100 mL), dried over anhydrous sodium sulfate and purified by silica gel column (petroleum ether/ethyl acetate, 50/1) to afford the title compound (6.8 g, 61%) as yellow oil.

후처리

  1. temperatureAfter cooled to room temperature
  2. customthe reaction mixture was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (100 ml×3)
  4. washwashed with brine (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. custompurified by silica gel column (petroleum ether/ethyl acetate, 50/1)

출처 및 근거

ORD 기록
ord-68193b27fb76400bb780747f2d739c08
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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