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

HRID 2304742Notes

Reaction equation

HRID 2304742 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 chromotography (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 chromotography (5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-d12b8ed5d0b74e28a82b216c7d57b616
Source dataset
uspto-grants-2002_08
Patent number
US06436982B1

Reaction notes

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