Dimethylformamide → 4-[(Heptyloxy)methoxy]-1-methyl-3,5-diphenyl-1H-pyrazole

HRID 1439130Notes

Reaction equation

HRID 1439130 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([OH:13])[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:3]1.C[O-].[Na+].CN([CH:26]=[O:27])C>>[CH2:15]([O:27][CH2:26][O:13][C:5]1[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:3][N:2]([CH3:1])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:14][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 12326421HCID 12326421, compound

Product 1

HCID 213981294-[(Heptyloxy)methoxy]-1-methyl-3,5-diphenyl-1H-pyrazole

Procedure

The temperature is maintained at -20° C to -10° C during the addition. When the exotherm subsides, the addition of gas is discontinued and the reaction mixture allowed to warm up to 5°-10° C. The reaction mixture is washed with chilled water (100 ml) and the organic layer separated. The organic layer is filtered through calcium chloride and added to a solution of the sodium salt of 1-methyl-3,5-diphenyl-4-pyrazolol in DMF. The 4-pyrazolol solution is prepared by stirring 1-methyl-3,5-diphenyl-4-pyrazolol (10 g, 0.04 mole) with sodium methoxide (2.16 g, 0.04 mole) and dry DMF (100 ml).

Workup

  1. temperatureThe temperature is maintained at -20° C to -10° C during the addition
  2. additionWhen the exotherm subsides, the addition of gas
  3. temperatureto warm up to 5°-10° C
  4. washThe reaction mixture is washed with chilled water (100 ml)
  5. customthe organic layer separated
  6. filtrationThe organic layer is filtered through calcium chloride
  7. additionadded to a solution of the sodium salt of 1-methyl-3,5-diphenyl-4-pyrazolol in DMF

Sources & evidence

ORD record
ord-d87a8dea64714177b090229c54fb965f
Source dataset
uspto-grants-1977_11
Patent number
US04058391

Reaction notes

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