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

HRID 976262Notes

Reaction equation

HRID 976262 reaction equation
[N:1]#[C:2][NH2:3].[F:4][C:5]([F:17])([O:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13])[CH:6]([F:8])[F:7].Cl.[N+:19]([O-:22])([O-:21])=[O:20].[NH4+]>C(O)C>[N+:19]([O-:22])([OH:21])=[O:20].[F:4][C:5]([F:17])([O:9][C:10]1[CH:11]=[C:12]([NH:13][C:2]([NH2:3])=[NH:1])[CH:14]=[CH:15][CH:16]=1)[CH:6]([F:7])[F:8]

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

10.1 g (240 mmol) of cyanamide (50% in water) are added to a suspension of 25.2 g (120 mmol) of 3-(1,1,2,2-tetrafluoro-ethoxy)-aniline in 125 ml of ethanol. 16.3 ml of hydrochloric acid (conc., 192 mmol) are then added to the brown solution and the reaction mixture is heated under reflux for 19 h. After cooling to RT, the reaction mixture is concentrated under reduced pressure and the residue is dissolved in 80 ml of water. After the addition of 19.2 g (240 mmol) of ammonium nitrate, the product is isolated by filtration, then washed with water and dried at 60° under I-HV. 3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl-guanidine nitrate is obtained; m.p. 132°-14133°.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 19 h
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. dissolutionthe residue is dissolved in 80 ml of water
  5. customthe product is isolated by filtration
  6. washwashed with water
  7. customdried at 60° under I-HV

Sources & evidence

ORD record
ord-bb0dbc9fdd464bcb80e1faf1d1bfc55f
Source dataset
uspto-grants-1997_03
Patent number
US05612340

Reaction notes

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