Acetic Acid → 4-amino-2-[2-(dimethylamino)-ethylamino]-1H-benzimidazole

HRID 2298811ノート

反応式

HRID 2298811 の反応式
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][NH:5][C:6]1[NH:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:14]([N+:15]([O-])=O)[C:8]=2[N:7]=1.C(O)(=O)C>C(O)C.[Fe]>[NH2:15][C:14]1[C:8]2[N:7]=[C:6]([NH:5][CH2:4][CH2:3][N:2]([CH3:18])[CH3:1])[NH:10][C:9]=2[CH:11]=[CH:12][CH:13]=1

参加物

5

反応物 2

HCID 176Acetic AcidHCID 183786772-[2-(dimethylamino)ethylamino]-4-nitro-1H-benzimidazole

生成物 1

HCID 183785624-amino-2-[2-(dimethylamino)-ethylamino]-1H-benzimidazole収率 86.6%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

To a solution of 2-[2-(dimethylamino)ethylamino]-4-nitro-1H-benzimidazole (105 mg) in ethanol (4 ml) were added iron (reduced, 118 mg) and acetic acid (0.24 ml) at room temperature and the mixture was refluxed for 6 hours. The precipitate was filtered off and the filtrate was evaporated in vacuo. The residue was dissolved in a mixture of chloroform and methanol (5-1) and the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution, and dried over magnesium sulfate. The solvent was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform-methanol-ammonia solution (28%)=160-32-1) to give 4-amino-2-[2-(dimethylamino)-ethylamino]-1H-benzimidazole (80 mg).

後処理

  1. temperaturethe mixture was refluxed for 6 hours
  2. filtrationThe precipitate was filtered off
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in a mixture of chloroform and methanol (5-1)
  5. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customThe residue was purified by preparative thin-layer chromatography (chloroform-methanol-ammonia solution (28%)=160-32-1)

出典と根拠

ORDレコード
ord-33439590b31344f0888e289ad4ded073
出典データセット
uspto-grants-2002_12
特許番号
US06495542B1

反応ノート

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