Nitric Acid → HCID 178418900, compound

HRID 8496

Reaction equation

HRID 8496 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[N:10]#[C:11][NH2:12].[N+:13]([O-:16])([OH:15])=[O:14]>C(O)C>[N+:13]([O-:16])([O-:15])=[O:14].[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:11]([NH2:12])=[NH2+:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7732P-AnisidineHCID 9864Cyanamide

Product 1

HCID 178418900HCID 178418900, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a room temperature solution of 4-methoxyaniline (10.0 g, 81.19 mmol) in ethanol (100 mL) was added cyanamide (7.24 mL, 50 wt % in water, 93.37 mmol) followed by the dropwise addition of concentrated nitric acid (5.71 mL). The mixture was heated at reflux for 3 hours and allowed to cool to room temperature. The resulting crystals were isolated on a filter to yield N-(4Methoxyphenyl)guanidinium nitrate (7.1 g, 38%) as a violet crystals. 1H NMR (DMSO-d6): δ 9.39 (s, 1 H), 7.22 (s, 3 H), 7.17 (d, 2 H), 6.99 (d, 2 H)<3.76 (s, 3 H); 13C NMR (DMSO-d6) δ 158.17, 156.26, 127.48, 127.27, 114.90, 55.40; MS m/z 166 (M+1 of free base).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customThe resulting crystals were isolated on
  4. filtrationa filter

Sources & evidence

ORD record
ord-1a0a39a08fc94f9eb7edeb3803282105
Source dataset
uspto-grants-2006_08
Patent number
US07087618B2

Linked notes

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