Nitric Acid → HCID 178418786, compound

HRID 1295878

Reaction equation

HRID 1295878 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);

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-5654adb650e24ed39806d12ce5159bec
Source dataset
uspto-grants-2007_07
Patent number
US07244740B2

Linked notes

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