Hydrochloric Acid → 3-(1,1,2,2-Tetrafluoroethoxy)phenylguanidine nitrate

HRID 440875Notes

Reaction equation

HRID 440875 reaction equation
[F:1][C:2]([F:14])([O:6][C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=1)[NH2:10])[CH:3]([F:5])[F:4].[N:15]#[C:16][NH2:17].Cl.[N+:19]([O-:22])([O-:21])=[O:20].[NH4+]>C(O)C>[N+:19]([O-:22])([OH:21])=[O:20].[F:1][C:2]([F:14])([O:6][C:7]1[CH:8]=[C:9]([NH:10][C:16]([NH2:17])=[NH:15])[CH:11]=[CH:12][CH:13]=1)[CH:3]([F:4])[F:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 22985Ammonium nitrateHCID 700233-(1,1,2,2-Tetrafluoroethoxy)aniline

Product 1

HCID 1785125183-(1,1,2,2-Tetrafluoroethoxy)phenylguanidine nitrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 25.2 g (120 mmol) of 3-(1,1,2,2-tetrafluoroethoxy)aniline in 125 ml of ethanol are added 10.1 g (240 mmol) of cyanamide (50% in water). Then 16.3 ml (192 mmol) of concentrated hydrochloric acid are added to the brown solution and the mixture is refluxed for 19 hours. After cooling to room temperature, the reaction mixture is concentrated under reduced pressure and the residue is dissolved in 80 ml of water. After addition of 19.2 g (240 mmol) of ammonium nitrate, the product is isolated by filtration, washed with water and dried at 60° C. under HV, giving 3-(1,1,2,2-tetrafluoroethoxy)phenylguanidine nitrate; m.p. 132°-134° C.

Workup

  1. temperaturethe mixture is refluxed for 19 hours
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in 80 ml of water
  4. customthe product is isolated by filtration
  5. washwashed with water
  6. customdried at 60° C. under HV

Sources & evidence

ORD record
ord-cd1da6e4307444ba85a59607f87eafb0
Source dataset
uspto-grants-1996_05
Patent number
US05521184

Reaction notes

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