Methyl iodide → 1-methyl-1H-1,3-benzodiazol-5-amine

HRID 429551

반응식

HRID 429551 반응식
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=1)([O-])=O.[H-].[Na+].[CH3:15]I.CO.[CH:19](Cl)(Cl)Cl>C1COCC1.CO.[Pd]>[CH3:19][N:8]1[C:7]2[CH:11]=[CH:12][C:4]([NH2:1])=[CH:5][C:6]=2[N:10]=[CH:9]1.[CH3:15][N:10]1[C:6]2[CH:5]=[C:4]([NH2:1])[CH:12]=[CH:11][C:7]=2[N:8]=[CH:9]1

참가 물질

9

반응물 4

HCID 6328Methyl iodideHCID 71955-NitrobenzimidazoleHCID 24758Sodium hydrideHCID 21584188Chloroform methanol

생성물 2

HCID 3154991-methyl-1H-1,3-benzodiazol-5-amine수율 21%HCID 136802831-Methyl-1H-benzimidazol-6-amine수율 11%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 5-nitrobenzimidazole (3.0 g, 18.4 mmol) in 100 ml of THF was stirred with NaH (2.7 g, 36.8 mmol) for 0.5 h at 25° C. To the solution was added methyl iodide (2.0 ml, 20.3 mmol) and resulting mixture was stirred for 12 h. The reaction mixture was concentrated in vacuo to provide an oil, which was dissolved in 200 ml of MeOH and stirred with 0.3 g of 10% Pd/C under H2 for 12 h. The reaction mixture was filtered and concentrated in vacuo, yielding a dark oily residue which was subjected to column chromatography (3% MeOH/CHCl3) to provide 0.69 g (3.9 mmol, 21%) of 1-methyl-5-aminobenzimidazole and 0.36 g (2.0 mmol, 11%) of 3-methyl-5-aminobenzimidazole.

후처리

  1. customresulting mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto provide an oil, which
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customyielding a dark oily residue which

출처 및 근거

ORD 기록
ord-27d1e517041d4ae195c0e0a0f32a5ef1
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316637B1

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