Nitric Acid → HCID 178432900, compound

HRID 1930593Notes

Reaction equation

HRID 1930593 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[N+]([O-])(O)=O.[N:18]#[C:19][NH2:20].C(OCC)C>C(O)C>[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:19]([NH2:20])=[NH:18])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 944Nitric Acid2×HCID 3283Diethyl EtherHCID 9864Cyanamide2×HCID 31574784-(2-methyl-1H-imidazol-1-yl)aniline

Product 1

HCID 178432900HCID 178432900, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-Methylimidazol-1-yl)phenylamine (10 g, 57.73 mmol) was dissolved in ethanol (100 mL). Nitric acid (3.96 mL, 57.73 mmol) was carefully added followed by cyanamide (2.427 g, 57.73 mmol). The reaction mixture was heated to reflux overnight. Extra cyanamide (1.942 g, 46.19 mmol) and nitric acid (2.98 mL, 46.19 mmol) were added and then the reaction mixture was refluxed for 16 hours. The reaction mixture was allowed to reach room temperature and ethyl ether (100 mL) was added. The mixture was refrigerated for 2 h and the solid obtained was filtered off and washed with ethyl ether yielding 1-(4-(2-methyl-1H-imidazol-1-yl)phenyl)guanidine (9.40 g, 76%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. temperaturethe reaction mixture was refluxed for 16 hours
  4. customto reach room temperature
  5. customthe solid obtained
  6. filtrationwas filtered off
  7. washwashed with ethyl ether

Sources & evidence

ORD record
ord-8eddb134579b471dab3754e5077aecd8
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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