Hydrazine hydrate (1:1) → HCID 22624549, compound

HRID 279165Notes

Reaction equation

HRID 279165 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])=[CH:17][CH:16]=3)[C:11]2=[O:29])=[CH:6][CH:5]=1)([O-])=O.O.NN>C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[CH:13][N:12]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]([F:27])([F:28])[CH:24]([F:25])[F:26])=[CH:19][CH:20]=3)[C:11]2=[O:29])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 22624545HCID 22624545, compound

Product 1

HCID 22624549HCID 22624549, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ferric chloride (0.2 g) and activated carbon (2.0 g) were added to a solution of 1-(4-nitrophenyl)-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (20.5 g) in methanol-tetrahydrofran (75 ml:75 ml), to which hydrazine hydrate (8.0 ml) was added dropwise over the period of 10 minutes. After the mixture was refluxed with stirring for 14 hours, ferric chloride (0.2 g), activated carbon (2.0 g) and hydrazine hydrate (8.0 ml) were added thereto and the reaction mixture was refluxed with stirring for further 6 hours. The activated carbon was filtered off and washed with methanol (100 ml). The filtrate and the washing were combined and distilled off under reduced pressure. The residue thus obtained was dissolved in ethyl acetate (700 ml). The ethyl acetate layer was washed with water (200 ml×4), dried over anhydrous magnesium sulfate and distilled off under reduced pressure to give 1-(4-aminophenyl)-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (18.1 g, 95%) as a pale yellow powder.

Workup

  1. additionwas added dropwise over the period of 10 minutes
  2. temperatureAfter the mixture was refluxed
  3. temperaturethe reaction mixture was refluxed
  4. stirringwith stirring for further 6 hours
  5. filtrationThe activated carbon was filtered off
  6. washwashed with methanol (100 ml)
  7. distillationdistilled off under reduced pressure
  8. customThe residue thus obtained
  9. washThe ethyl acetate layer was washed with water (200 ml×4)
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationdistilled off under reduced pressure

Sources & evidence

ORD record
ord-3c23a101c1d74a148a3110f9a6deb2e6
Source dataset
uspto-grants-2002_03
Patent number
US06362206B1

Reaction notes

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