p-Toluenesulfonic acid → HCID 59210396, compound

HRID 2243262Notes

Reaction equation

HRID 2243262 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3](=O)[CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13]([CH3:20])[CH:12]=1)[C:5](OCC)=[O:6].O.[NH2:25][NH2:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:20][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[N+:17]([O-:19])=[O:18])[CH2:10][CH:4]1[C:3]([C:2]([F:23])([F:22])[F:1])=[N:26][NH:25][C:5]1=[O:6]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 24654Hydrazine hydrate (1:1)HCID 59210383HCID 59210383, compound

Product 1

HCID 59210396HCID 59210396, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 4,4,4-trifluoro-2-(3-methyl-4-nitro-benzyl)-3-oxo-butyrate (2.0 g), hydrazine monohydrate (0.5 g) and a small amount of p-toluenesulfonic acid were dissolved in toluene, and the mixture was refluxed for 4 hours. After cooling, the solvent was distilled off under reduced pressure. The residue was suspended in ethyl acetate and washed with 1N aqueous solution of hydrochloric acid. After drying the organic layer with sodium sulfate, the solvent was distilled off and the obtained residue was purified by silica gel column chromatography to obtain 4-(3-methyl-4-nitro-benzyl)-5-trifluoromethyl-2,4-dihydro-pyrazol-3-one (1.0 g).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off under reduced pressure
  4. washwashed with 1N aqueous solution of hydrochloric acid
  5. dry with materialAfter drying the organic layer with sodium sulfate
  6. distillationthe solvent was distilled off
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f1fb38fb7ca94ea48e82ff0bdc38bf35
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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