N-Phenylhydroxylamine → 1-Trifluoromethyl-3-phenyl-3-hydroxyurea

HRID 267675

Reaction equation

HRID 267675 reaction equation
[F:1][C:2]([N:5]=[C:6]=[O:7])([F:4])[F:3].[C:8]1([NH:14][OH:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCCCC>C(OCC)C>[F:1][C:2]([F:4])([F:3])[NH:5][C:6]([N:14]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[OH:15])=[O:7]

Participants

5

Reactant 3

HCID 7518N-PhenylhydroxylamineHCID 8003PentaneHCID 12494313Trifluoromethyl isocyanate

Product 1

HCID 215536781-Trifluoromethyl-3-phenyl-3-hydroxyurea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of trifluoromethyl isocyanate (11.1 grams, 0.1 mol) in diethyl ether (35 ml) is added dropwise, with stirring to a solution of N-phenyl hydroxylamine (10.9 grams; 0.1 mol) in ether (60 ml) at room temperature. Stirring is continued for a period of about 1 hour resulting in a precipitate. Pentane is added to the mixture to form additional precipitate. The precipitate is then recovered by filtration, is washed and dried to yield 1-trifluoromethyl-3-phenyl-3-hydroxyurea.

Workup

  1. customresulting in a precipitate
  2. customto form additional precipitate
  3. filtrationThe precipitate is then recovered by filtration
  4. washis washed
  5. customdried

Sources & evidence

ORD record
ord-92f7c705668c44ad969cff59709360de
Source dataset
uspto-grants-1976_03
Patent number
US03944410

Linked notes

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