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

HRID 1636683Notes

Reaction equation

HRID 1636683 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-fb8232a4410a42deb8a0113570c1b93c
Source dataset
uspto-grants-2000_03
Patent number
US06034248

Reaction notes

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