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Methyl iodide → 5-(3-Chloro-5-trifluoromethylpyridin-2-yl)-3-methyl-1-(1-methylethyl)benzimidazol-2-one

HRID 1276081
ノート
印刷プレビュー

反応式

HRID 1276081 の反応式
[H-].[Na+].[Cl:3][C:4]1[C:5]([C:14]2[CH:26]=[CH:25][C:17]3[N:18]([CH:22]([CH3:24])[CH3:23])[C:19](=[O:21])[NH:20][C:16]=3[CH:15]=2)=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.[CH3:27]I>CN(C)C=O>[Cl:3][C:4]1[C:5]([C:14]2[CH:26]=[CH:25][C:17]3[N:18]([CH:22]([CH3:23])[CH3:24])[C:19](=[O:21])[N:20]([CH3:27])[C:16]=3[CH:15]=2)=[N:6][CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 221148555-(3-Chloro-5-trifluoromethylpyridin-2yl)-1-(1-methylethyl)benzimidazol-2-one

生成物 1

HCID 221148405-(3-Chloro-5-trifluoromethylpyridin-2-yl)-3-methyl-1-(1-methylethyl)benzimidazol-2-one収率 80.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

0.23 g of an 80% strength by weight suspension of sodium hydride in mineral oil was added at 23° C. to 25 ml of anhydrous dimethylformamide. The mixture was then treated dropwise with a solution of 2.50 g of 5-(3-chloro-5-trifluoromethylpyridin-2-yl)-1-(1-methylethyl)benzimidazol-2-one in 25 ml of dimethylformamide and, after stirring for 15 minutes, with 1.05 g of methyl iodide. After stirring for 6 hours, the reaction mixture was poured into 300 ml of ice water. The aqueous phase was extracted three times with 100 ml of tert-butyl methyl ether each time, after which the combined organic phases were washed twice with 50 ml of water each time, dried over sodium sulfate and concentrated. Chromatography on silica gel using cyclohexane/ethyl acetate (4:1) as the eluent gave 2.1 g of colorless crystals. Yield: 75%; m.p.: 108-109° C.

後処理

  1. extractionThe aqueous phase was extracted three times with 100 ml of tert-butyl methyl ether each time
  2. washafter which the combined organic phases were washed twice with 50 ml of water each time
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-89d3a59ec259467bac3a8888db981c72
出典データセット
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06165941

反応ノート

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