Ethanol → 7-Amino-5-cyano-1-phenylbenzimidazole

HRID 644556Notes

Reaction equation

HRID 644556 reaction equation
[C:1]1([NH:7][C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][C:11]([C:17]#[N:18])=[CH:10][C:9]=2[N+:19]([O-])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[Sn]Cl.[CH2:25](O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(O)=O>[NH2:14][C:13]1[C:8]2[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:25]=[N:19][C:9]=2[CH:10]=[C:11]([C:17]#[N:18])[CH:12]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 85829898N-phenyl-4-cyano-2,6-dinitroaniline

Product 1

HCID 674850457-Amino-5-cyano-1-phenylbenzimidazoleYield 64%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a stirred suspension of N-phenyl- 4-cyano-2,6-dinitroaniline (16.4 g, 57.8 mmol) and SnCl2, 2H2O (130.5 g, 0.58 mol) in abs. ethanol (300 ml) was added formic acid (90 ml) dropwise at ambient temperature. The reaction is exothermic. The reaction was allowed to proceed at ambient conditions overnight. The resultant mixture was rendered alkaline by addition of saturated, aqueous sodium carbonate and was filtered through Celite. The filtrate was extracted with dichloromethane. The organic extract was dried over magnesium sulphate and evaporated under reduced pressure. The residue was triturated in cold ethyl acetate to leave the title product (8.65 g, 64%).

Workup

  1. customto proceed at ambient conditions overnight
  2. filtrationwas filtered through Celite
  3. extractionThe filtrate was extracted with dichloromethane
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. customThe residue was triturated in cold ethyl acetate

Sources & evidence

ORD record
ord-2d81a339e5ac4a4cbb60abb9938651a2
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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