Sodium hydride → 1-Methyl-3,5-diphenyl-4-propoxy-1H-pyrazole

HRID 1658392Notes

Reaction equation

HRID 1658392 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:7]([OH:15])[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5]1.I[CH2:23][CH2:24][CH3:25]>CCOCC>[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:7]([O:15][CH2:23][CH2:24][CH3:25])[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 12326421HCID 12326421, compound

Product 1

HCID 213981171-Methyl-3,5-diphenyl-4-propoxy-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (57%, 0.92 g, 0.022 mole) is added slowly to a suspension of 1-methyl-3,5-diphenyl-4-pyrazolol (5 g, 0.02 mole) in anhydrous ether (100 ml). An off-white precipitate forms. After stirring for 45 minutes, the solid is removed by filtration, added to dry DMF (30 ml) and treated with 1-iodopropane (5 ml, 0.05 mole). The reaction mixture is stirred, heated at 60°C for 14 hours and then poured into ice water (600 ml). After standing for 24 hours in the refrigerator, a tacky yellow solid is formed. Recrystallization from hexane at -20°C affords an off-white solid, melting point 56°-57°C.

Workup

  1. customthe solid is removed by filtration
  2. additionadded to dry DMF (30 ml)
  3. stirringThe reaction mixture is stirred
  4. waitAfter standing for 24 hours in the refrigerator
  5. customa tacky yellow solid is formed
  6. customRecrystallization from hexane at -20°C
  7. customaffords an off-white solid, melting point 56°-57°C.

Sources & evidence

ORD record
ord-b4a5ef3a4c714923888604886afaed89
Source dataset
uspto-grants-1976_06
Patent number
US03963742

Reaction notes

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