3,5-Dimethylpyrazole → 3,5-Dimethyl-1-octyl-1H-pyrazole

HRID 1834998Notes

Reaction equation

HRID 1834998 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][N:3]=1.[Na].[H][H].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>O1CCCC1>[CH2:12]([N:3]1[C:2]([CH3:1])=[CH:6][C:5]([CH3:7])=[N:4]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 62103,5-DimethylpyrazoleHCID 81401-BromooctaneHCID 5360545SodiumHCID 178418361HCID 178418361, compound

Product 1

HCID 5730813,5-Dimethyl-1-octyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Octyl-3,5-dimethylpyrazole was prepared in the following manner. All manipulations were performed under a nitrogen atmosphere. 3,5-Dimethylpyrazole (5 g) was placed in a 100-mL 3-neck round-bottom flask with a magnetic stir bar and dissolved in 50 mL tetrahydrofuran. A condenser and stoppers were added. Sodium metal (1.2 g) was added in pieces. Hydrogen evolution was evident. Mixture was stirred at room temperature overnight. 1-Bromooctane (9 mL) was then added all at once. The mixture was brought to a gentle reflux for seven hours and then stirred overnight at room temperature. The reaction mixture was filtered through a sintered-glass frit to remove a white precipitate. Solvent was removed under vacuum. Product was distilled under vacuum. The fractions distilling at 65-70° C. were collected and used in subsequent preparations.

Workup

  1. additionA condenser and stoppers were added
  2. temperaturea gentle reflux for seven hours
  3. stirringstirred overnight at room temperature
  4. filtrationThe reaction mixture was filtered through a sintered-glass frit
  5. customto remove a white precipitate
  6. customSolvent was removed under vacuum
  7. distillationProduct was distilled under vacuum
  8. distillationThe fractions distilling at 65-70° C.
  9. customwere collected

Sources & evidence

ORD record
ord-f910618821bf4d348871741ac37f5b47
Source dataset
uspto-grants-2004_08
Patent number
US06770122B2

Reaction notes

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