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

HRID 1398758ノート

反応式

HRID 1398758 の反応式
[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

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 31398ChlorosuccinimideHCID 68760821HCID 68760821、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-68193b27fb76400bb780747f2d739c08
出典データセット
uspto-grants-2014_12
特許番号
US08901141B2

反応ノート

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