Methanol → 3,5-Diphenyl-4-propoxy-1H-pyrazole

HRID 1974357Notes

Reaction equation

HRID 1974357 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.Br[CH2:25][CH2:26][CH3:27]>O>[CH2:25]([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)[CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 78401-BromopropaneHCID 3149543,5-diphenyl-1H-pyrazol-4-olHCID 10942334Sodium Methoxide

Product 1

HCID 213980993,5-Diphenyl-4-propoxy-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 1-bromopropane (5.17 g, 0.042 mole) is added slowly (5 minutes) at 60° C. The reaction mixture is then held at 60° C until the reaction is complete by tlc. The mixture is poured into water and the solid formed isolated by filtration. Recrystallization of the solid from acetonitrile affords white crystals, 7.4 g (63%), melting point 142°-142.5° C.

Workup

  1. customis then held at 60° C until the reaction
  2. customthe solid formed
  3. customisolated by filtration
  4. customRecrystallization of the solid from acetonitrile
  5. customaffords white crystals, 7.4 g (63%), melting point 142°-142.5° C.

Sources & evidence

ORD record
ord-f79f4047be0244d09108ec0dc19cd45d
Source dataset
uspto-grants-1976_12
Patent number
US04000301

Reaction notes

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