2,5-Hexanedione → 7-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 1698550ノート

反応式

HRID 1698550 の反応式
[NH2:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:13][C:14](=O)[CH2:15][CH2:16][C:17](=O)[CH3:18].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:18][C:17]1[N:1]([C:2]2[C:7]3[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=3[CH:5]=[CH:4][CH:3]=2)[C:14]([CH3:13])=[CH:15][CH:16]=1

参加物

5

反応物 3

HCID 80352,5-HexanedioneHCID 516892Sodium BicarbonateHCID 596354197-Amino-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

生成物 1

HCID 672731377-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one収率 68.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

To a suspension of 257 mg (1.57 mmol) of 7-amino-1-methyl-1,3-dihydro-2H-benzimidazol-2-one in 2 mL of acetic acid was added 0.18 mL (1.57 mmol) of 2,5-hexanedione, the mixture was stirred at 90° C. for 1 hour. After cooling, the reaction mixture was neutralized by saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 25-50% ethylacetate/n-hexane gradient mixture to give 258 mg (68%) of the title compound.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (X2)
  3. washThe combined organic layer was washed with brine (X1)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a 25-50% ethylacetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-d60e54c0ab7f42a5b2bacd754876cdb7
出典データセット
uspto-grants-2012_04
特許番号
US08163935B2

反応ノート

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