Methanol → 4-(Benzyloxy)-3,5-diphenyl-1H-pyrazole

HRID 436609Notes

Reaction equation

HRID 436609 reaction equation
[C:1]1([C:7]2[C:11]([OH:12])=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].CO.[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([O:12][C:11]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:8][NH:9][C:10]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7503Benzyl ChlorideHCID 3149543,5-diphenyl-1H-pyrazol-4-olHCID 10942334Sodium Methoxide

Product 1

HCID 213980924-(Benzyloxy)-3,5-diphenyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3,5-diphenyl-4-pyrazolol (10 g, 0.042 mole), sodium methoxide (2.27 g, 0.042 mole) and methanol (60 ml) is heated at 60° C for 2 hours. Then benzyl chloride is added slowly at 60° C. A white solid forms. Heating is continued overnight at 60° C. The reaction mixture is examined by glc and the reaction is found to be complete. The mixture is poured into water and the solid isolated by filtration. The solid is washed well with water, dried and recrystallized from acetonitrile to give pale yellow crystals, melting point 152°-152.5° C.

Workup

  1. temperatureHeating
  2. customthe solid isolated by filtration
  3. washThe solid is washed well with water
  4. customdried
  5. customrecrystallized from acetonitrile
  6. customto give pale yellow crystals, melting point 152°-152.5° C.

Sources & evidence

ORD record
ord-26a46b394f8c4bcb9d094c10cb4dc312
Source dataset
uspto-grants-1977_02
Patent number
US04009277

Reaction notes

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