Nitric Acid → 4-Fluorophenylguanidine nitrate

HRID 47200Notes

Reaction equation

HRID 47200 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N+:9]([O-:12])([OH:11])=[O:10].[N:13]#[C:14][NH2:15]>CCO>[N+:9]([O-:12])([OH:11])=[O:10].[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14]([NH2:15])=[NH:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 97314-FluoroanilineHCID 9864Cyanamide

Product 1

HCID 1785125564-Fluorophenylguanidine nitrateYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-fluoroaniline (25 mmol, 2.80 g) in EtOH (10 mL) was cooled on an ice bath. Nitric acid (69% aq. soln.; 1.8 mL) was added dropwise. Then cyanamide (50% aq. soln.; 4 mL) was added. The reaction mixture was refluxed under N2 for 21 h. The solvent was evaporated to dryness. The solid residue was washed with EtOH and dried under high vacuum overnight to afford the title compound as a purple powder (2.54 g, 47%). This material was used for subsequent reaction without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed under N2 for 21 h
  2. customThe solvent was evaporated to dryness
  3. washThe solid residue was washed with EtOH
  4. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-b6ab4688792140cda6c30a454fe08d05
Source dataset
uspto-grants-2004_03
Patent number
US06699854B2

Reaction notes

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