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

HRID 2299159Notes

Reaction equation

HRID 2299159 reaction equation
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.CCO>C(OC(=O)C)(=O)C.Cl.[Pd]>[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

Participants

8

Reactant 4

HCID 284Formic AcidHCID 702EthanolHCID 190526-Chloro-2,4-dinitroanilineHCID 178522168HCID 178522168, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
25 °C

Procedure

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 foramide was dissolved in 20 ml of HCl sat'd EtOH and stirred for 3 h 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.

Workup

  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)

Sources & evidence

ORD record
ord-b67b13454c5c47fba527c8b1ec7bfac7
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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