2-Nitro-1H-benzimidazole → 2-cyclopropyl-1H-benzimidazol-5-amine

HRID 429572

반응식

HRID 429572 반응식
[N+](C1C=CC(N)=C(N)C=1)([O-])=O.[CH:12]1([C:15]2[NH:16][C:17]3[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:14][CH2:13]1.[N+](C1NC2C=CC=CC=2N=1)([O-])=O>C1(C(O)=O)CC1.CCOC(C)=O.CO.[Pd]>[CH:12]1([C:15]2[NH:16][C:17]3[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:14][CH2:13]1

참가 물질

8

반응물 3

HCID 972342-Nitro-1H-benzimidazoleHCID 51117914-Nitro-1,2-phenylenediamineHCID 162275222-cyclopropyl-5-nitro-1H-1,3-benzodiazole

생성물 1

HCID 183798632-cyclopropyl-1H-benzimidazol-5-amine수율 75%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매HCID 15655Cyclopropanecarboxylic acid용매

실험 절차

A solution of 4-nitro-1,2-phenylenediamine (1.0 g, 6.6 mmol) in 15 ml of cyclopropanecarboxylic acid was stirred at reflux for 12 h. The reaction mixture was concentrated in vacuo to yield a oil, 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-cyclopropyl-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 MeOH and stirred for 12 h under H2. The reaction mixture was filtered and concentrated in vacuo to provide 0.87 g (4.9 mmol, 75%) of the desired product.

후처리

  1. temperatureat reflux for 12 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto yield a oil, 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-2bb41960faa840e89d317706c0c3bcd6
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316637B1

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