Hydrazine → HCID 20349091, compound

HRID 1449312Notes

Reaction equation

HRID 1449312 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.[CH3:22][N:23]=[C:24]=[O:25]>O1CCCC1.[Pd]>[CH3:22][NH:23][C:24]([N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[OH:10])=[O:25]

Participants

7

Reactant 4

HCID 9321HydrazineHCID 9590p-FluoronitrobenzeneHCID 12228Methyl IsocyanateHCID 164595Benzenamine, 4-fluoro-N-hydroxy-

Product 1

HCID 20349091HCID 20349091, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

p-Fluoronitrobenzene (14.1 g; 0.1 mole) was dissolved in tetrahydrofuran (100 ml.). Ten percent palladium on charcoal catalyst (0.1 g.) was added to the solution followed by hydrazine (6.0 ml; 0.105 mole), and the resulting mixture stirred at room temperature for about 48 hours with cooling as necessary. The reaction mixture containing N-(4-fluorophenyl) hydroxylamine was dried over anhydrous magnesium sulfate and filtered. To this solution was added methyl isocyanate (6.2 ml; 0.1 mole) and the mixture stirred for about 15 minutes. The reaction mixture was concentrated by distilling and then washed with hexane and filtered to yield 1-methyl-3-(4'-fluorophenyl)-3-hydroxyurea as a yellow solid.

Workup

  1. temperaturewith cooling as necessary
  2. dry with materialwas dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. stirringthe mixture stirred for about 15 minutes
  5. concentrationThe reaction mixture was concentrated
  6. distillationby distilling
  7. washwashed with hexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-7931ff4facb74a0997b0b6f52beda03e
Source dataset
uspto-grants-1980_02
Patent number
US04190431

Reaction notes

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