Hydrazine → 1-Trifluoromethyl-3-(4'-fluorophenyl)-3-hydroxyurea

HRID 267677Notes

Reaction equation

HRID 267677 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=O)=[CH:4][CH:3]=1.NN.FC1C=CC(NO)=CC=1.[F:22][C:23]([N:26]=[C:27]=[O:28])([F:25])[F:24]>O1CCCC1.[Pd]>[F:22][C:23]([F:25])([F:24])[NH:26][C:27]([N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[OH:10])=[O:28]

Participants

7

Reactant 4

HCID 9321HydrazineHCID 9590p-FluoronitrobenzeneHCID 164595Benzenamine, 4-fluoro-N-hydroxy-HCID 12494313Trifluoromethyl isocyanate

Product 1

HCID 215536861-Trifluoromethyl-3-(4'-fluorophenyl)-3-hydroxyurea

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

p-Fluoronitrobenzene (14.1 grams; 0.1 mol) is dissolved in tetrahydrofuran (100 ml). Ten percent palladium on charcoal catalyst (0.1 gram) is added to the solution followed by hydrazine (6.0 ml; 0.1 mol), and the resulting mixture stirred at room temperature for about 48 hours with cooling as necessary. The reaction mixture, containing N-(4-fluorophenyl)hydroxylamine, is dried over anhydrous magnesium sulfate and filtered. To this solution is added trifluoromethyl isocyanate (11.1 grams; 0.1 mol) and the solution is stirred for about 15 minutes. The reaction mixture is concentrated by evaporation of solvent and the resulting precipitate is recovered by filtration to yield 1-trifluoromethyl-3-(4'-fluorophenyl)-3-hydroxyurea.

Workup

  1. temperaturewith cooling as necessary
  2. dry with materialis dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. stirringthe solution is stirred for about 15 minutes
  5. concentrationThe reaction mixture is concentrated by evaporation of solvent
  6. filtrationthe resulting precipitate is recovered by filtration

Sources & evidence

ORD record
ord-0602c3d4e9bc4c668329009b7e253eb4
Source dataset
uspto-grants-1976_03
Patent number
US03944410

Reaction notes

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