Dibenzoylmethane → 1H-Pyrazole, 3,5-diphenyl-

HRID 1373773Notes

Reaction equation

HRID 1373773 reaction equation
O.[NH2:2][NH2:3].[C:4]1([C:10](=O)[CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[C:4]1([C:10]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:3][N:2]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 8433DibenzoylmethaneHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 708401H-Pyrazole, 3,5-diphenyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Hydrazine monohydrate (2.16 mL) is added to a solution of 1,3-diphenylpropane-1,3-dione (10.0 g) in ethanol (100 mL) and the mixture is heated to 60° C. for 2.5 h forming a white precipitate over this time. Ethanol is removed in vacuo and the residue is taken up in ethyl acetate. The resulting suspension is filtered to give 3,5-diphenyl-1H-pyrazole, 22 (3.44 g) as a white powder. The filtrate is washed with water (2×100 mL), dried over magnesium sulfate and concentrated to give further 3,5-diphenyl-1H-pyrazole, 22 (5.90 g) as a solid.

Workup

  1. customforming a white precipitate over this time
  2. customEthanol is removed in vacuo
  3. filtrationThe resulting suspension is filtered

Sources & evidence

ORD record
ord-21e3d137fcdc44e8ab4e610a77a4c66b
Source dataset
uspto-grants-2007_01
Patent number
US07163945B2

Reaction notes

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