N'-(6-Cyano-3-methyl-2,4-dinitro-phenyl)-N,N-dimethyl-methanimidamide → HCID 178430523, compound

HRID 968788Notes

Reaction equation

HRID 968788 reaction equation
[C:1]([C:3]1[C:8]([N:9]=[CH:10]N(C)C)=[C:7]([N+:14]([O-])=O)[C:6]([CH3:17])=[C:5]([N+:18]([O-])=O)[CH:4]=1)#[N:2]>[Pd].CO>[NH2:18][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[C:8]2[N:9]=[CH:10][NH:14][C:7]=2[C:6]=1[CH3:17]

Participants

4

Reactant 1

HCID 59016305N'-(6-Cyano-3-methyl-2,4-dinitro-phenyl)-N,N-dimethyl-methanimidamide

Product 1

HCID 178430523HCID 178430523, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N′-(6-cyano-3-methyl-2,4-dinitro-phenyl)-N,N-dimethyl-methanimidamide (8) (0.607 g, 2.42 mmol) and 10% palladium on carbon (0.23 g of 50% water wet) and methanol (60 mL) is agitated under hydrogen pressure (43 psi) for about 4.5 hours. The vessel is then flushed with nitrogen and the mixture is heated to 60° C. for about 2.5 hours. The mixture is allowed to cool to ambient temperature and is then filtered through a pad of Celite. The solvent is then evaporated in vacuo to provide 6-Amino-7-methyl-1H-benzimidazole-4-carbonitrile (10) (0.426 g, >100% crude Yield), as a brown solid.

Workup

  1. customThe vessel is then flushed with nitrogen
  2. temperatureto cool to ambient temperature
  3. filtrationis then filtered through a pad of Celite
  4. customThe solvent is then evaporated in vacuo

Sources & evidence

ORD record
ord-80b7e7436e144163af9fee8ac0584584
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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