Nitric Acid → HCID 178418786, compound

HRID 896769

Reaction equation

HRID 896769 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]#[C:9][NH2:10].[N+:11]([O-:14])([OH:13])=[O:12]>C(O)C>[N+:11]([O-:14])([O-:13])=[O:12].[C:2]1([NH:1][C:9]([NH2:10])=[NH2+:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 6115AnilineHCID 9864Cyanamide

Product 1

HCID 178418786HCID 178418786, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a room temperature solution of aniline (10.0 g, 107 mmol) in ethanol (100 mL) was added cyanamide (9.6 mL, 50 wt % in water, 123 mmol) followed by the dropwise addition of concentrated nitric acid (7.56 mL). The mixture was heated at reflux for 3.5 hours and allowed to cool to room temperature. The mixture was concentrated in vacuo and the residue was crystallized from methanol/ethyl acetate/dichloromethane to yield N-phenylguanidinium nitrate (6.7 g, 32%) as a white crystalline solid. 1H NMR (DMSO-d6): δ 9.63 (s, 1 H), 7.44 (t, 2 H), 7.37 (broad s, 3 H), 7.29 (t, 1 H), 7.23 (d, 2 H); 13C NMR (DMSO-d6): δ 156.36, 135.99, 130.40, 127.19, 125.18; MS m/z 136 (M+1 of free base).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3.5 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was crystallized from methanol/ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-a7dd97df1217456a9e1a92f3999a5de5
Source dataset
uspto-grants-2005_07
Patent number
US06919352B2

Linked notes

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