Methane → 3H-Pyrazol-3-one, 2,4-dihydro-2,5-diphenyl-

HRID 1289836Notes

Reaction equation

HRID 1289836 reaction equation
F[C:2](F)(F)[C:3](=O)[CH2:4][C:5]([O:7]CC)=O.Cl[C:14]1[CH:19]=[CH:18][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1.Cl.[CH4:23]>CO>[C:17]1([N:20]2[C:5](=[O:7])[CH2:4][C:3]([C:2]3[CH:5]=[CH:4][CH:3]=[CH:2][CH:23]=3)=[N:21]2)[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 70624(4-Chlorophenyl)hydrazine

Product 1

HCID 785593H-Pyrazol-3-one, 2,4-dihydro-2,5-diphenyl-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 10 g (54.3 mmol) of ethyl trifluoroacetoacetate and 9.72 g (54.3 mmol) of 4-chlorophenylhydrazine and 1 mL of concentrated HCl in 130 ml of methanol was refluxed with stirring for 22 hours. After adding activated charcoal with stirring, the hot mixture was filtered, diluted with water, and the resulting white solid was filtered. The solid was washed with hexane and dried to afford 19 g of 2,4-dihydro-2-(4-chlorophenyl)-5-trifluoromethyl-3H-2-pyrazol-3-one (Formula III: R1 =4-Cl--Ph; R2 =CF3 ; R3 =H) as a white solid.

Workup

  1. temperaturewas refluxed
  2. stirringwith stirring
  3. filtrationthe hot mixture was filtered
  4. additiondiluted with water
  5. filtrationthe resulting white solid was filtered
  6. washThe solid was washed with hexane
  7. customdried

Sources & evidence

ORD record
ord-69f824dfd3df4a458167a28d27f23094
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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