2-Nitro-1H-benzimidazole → 2-Isopropyl-1H-benzo[d]imidazol-5-amine

HRID 429567

반응식

HRID 429567 반응식
[N+](C1C=CC(N)=C(N)C=1)([O-])=O.[CH:12]([C:15]1[NH:16][C:17]2[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:18]=2[N:19]=1)([CH3:14])[CH3:13].[N+](C1NC2C=CC=CC=2N=1)([O-])=O>C(O)(=O)C(C)C.CCOC(C)=O.[Pd]>[CH:12]([C:15]1[NH:16][C:17]2[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][C:18]=2[N:19]=1)([CH3:14])[CH3:13]

참가 물질

7

반응물 3

HCID 972342-Nitro-1H-benzimidazoleHCID 6832022-Isopropyl-5-nitro-1H-benzo[d]imidazoleHCID 51117914-Nitro-1,2-phenylenediamine

생성물 1

HCID 8207492-Isopropyl-1H-benzo[d]imidazol-5-amine수율 92%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 6590Isobutyric Acid용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-nitro-1,2-phenylenediamine (0.9 g, 5.9 mmol) in 5 ml of isobutyric acid was stirred at reflux for 12 h. The reaction mixture was concentrated in vacuo to yield a dark brown residue, which was dissolved in 100 ml of EtOAc and washed with aqueous NaHCO3. Organic layer was dried over MgSO4 and concentrated in vacuo, yielding an oil which was characterized as 2-isopropyl-5-nitrobenzimidazole and subjected to a following reaction without further purification. The nitrobenzimidazole and 50 mg of 10% Pd—C were dissolved in 100 ml of MeOR and stirred for 12 h under H2. The reaction mixture was filtered and concentrated in vacuo, yielding 0.95 g (5.4 mmol, 92%) of the desired product.

후처리

  1. temperatureat reflux for 12 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto yield a dark brown residue, which
  4. washwashed with aqueous NaHCO3
  5. dry with materialOrganic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customyielding an oil which
  8. customsubjected to a following reaction without further purification
  9. filtrationThe reaction mixture was filtered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a0acbcf57354477087623ad8fa15df60
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316637B1

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