Formic Acid → 7-Chloro-1H-benzo[d]imidazol-5-amine

HRID 429580

반응식

HRID 429580 반응식
ClC1C(N)=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1.C(O)=O.[Cl:18][C:19]1[C:27]2[NH:26][CH:25]=[N:24][C:23]=2[CH:22]=[C:21]([NH:28]C=O)[CH:20]=1.C(N)=O>C(OC(=O)C)(=O)C.Cl.[Pd].CCO>[Cl:18][C:19]1[C:27]2[NH:26][CH:25]=[N:24][C:23]=2[CH:22]=[C:21]([NH2:28])[CH:20]=1

참가 물질

9

반응물 4

HCID 284Formic AcidHCID 713FormamideHCID 190526-Chloro-2,4-dinitroanilineHCID 178522168HCID 178522168, 화합물

생성물 1

HCID 1785076737-Chloro-1H-benzo[d]imidazol-5-amine

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 313Hydrochloric Acid용매HCID 702Ethanol용매HCID 7918Acetic Anhydride용매

실험 절차

Methanolic solution of 6-chloro-2,4-dinitroaniline (2.4 g, 11 mmol) was stirred overnight with 100 mg of 10% Pd/C under H2. Reaction mixture was filtered and concentrated in vacuo to provide an oil which was dissolved in 10 ml of acetic anhydride and 10 ml of formic acid and stirred at reflux for 12 h. The reaction mixture was concentrated in vacuo, yielding a brown oil which was characterized as 4-chloro-6-foramidylbenzimidazole in NMR analysis. The formamide was dissolved in 20 ml of HCl sat'd EtOH and stirred for 3h at 25° C. The reaction mixture was purified in column chromatography (5% MeOH/EtOAc) to provide 0.89 g (5.3 mmol, 48% overall) of the desired product.

후처리

  1. customReaction mixture
  2. filtrationwas filtered
  3. concentrationconcentrated in vacuo
  4. customto provide an oil which
  5. temperatureat reflux for 12 h
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. customyielding a brown oil which
  8. customThe reaction mixture was purified in column chromatography (5% MeOH/EtOAc)

출처 및 근거

ORD 기록
ord-98b5b6c4ca6e4c908c7280faa5b61774
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316637B1

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