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

HRID 2304744Notes

Reaction equation

HRID 2304744 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 reflux 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 oily residue which

Sources & evidence

ORD record
ord-ca339561a2164b4688afbd4c8204fc0c
Source dataset
uspto-grants-2002_08
Patent number
US06436982B1

Reaction notes

Loading…