Hydrochloric Acid → 7-Iodo-1H-benzimidazol-5-amine

HRID 2299161Notes

Reaction equation

HRID 2299161 reaction equation
O.O.Cl[Sn]Cl.Cl.[N+:7]([C:10]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[C:13]([I:20])[C:11]=1[NH2:12])([O-])=O.[OH-].[Na+].CO.[CH3:25]COC(C)=O>>[I:20][C:13]1[C:11]2[N:12]=[CH:25][NH:7][C:10]=2[CH:16]=[C:15]([NH2:17])[CH:14]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 183798712-Iodo-4,6-dinitroanilineHCID 21584119Ethylacetate methanol

Product 1

HCID 183798487-Iodo-1H-benzimidazol-5-amineYield 33%

Procedure

A solution of 10 g of SnCl2.2H2O and 20 ml of HCl was added into 2,4-dinitro-6-iodoaniline (4.1 g, 13 mmol) and resulting reaction mixture was stirred at reflux for 48 h. The reaction mixture was then basified by adding 15% aq. NaOH and extracted with CHCl3 several times. Combined extracts were dried over MgSO4 and concentrated in vacuo, yielding. oily residue which was subjected to column chromatography (5% MeOH/EtOAc) to yield 1.1 g (4.4 mmol, 33%) of the amine. The amine was stirred at ref lux in 10 ml of formic acid and 10 ml of acetic anhydride for 12 h. The reaction mixture was concentrated in vacuo to yield an oily residue which was stirred in 30 ml of HCl sat'd EtOH for 2 h. The oily reaction mixture after concentration was subjected to column chromatography (5% NH3 sat'd MeOH/EtOAc) to provide 0.69 g (2.7 mmol, 60%) of the desired product.

Workup

  1. customresulting
  2. customreaction mixture
  3. temperatureat reflux for 48 h
  4. extractionextracted with CHCl3 several times
  5. dry with materialCombined extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customyielding

Sources & evidence

ORD record
ord-ec272c038c8f48bb8c7b101fca396e99
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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