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

HRID 2298811노트

반응식

HRID 2298811 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-33439590b31344f0888e289ad4ded073
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495542B1

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