Triethylamine → 3,5-Diethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazole

HRID 1740099Notes

Reaction equation

HRID 1740099 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[NH:11][NH2:12].[CH3:13][CH2:14][C:15](=O)[CH2:16][C:17](=O)[CH2:18][CH3:19].C(N(CC)CC)C>C(O)C>[CH2:14]([C:15]1[CH:16]=[C:17]([CH2:18][CH3:19])[N:11]([C:4]2[C:3]([CH3:2])=[CH:8][C:7]([CH3:9])=[CH:6][C:5]=2[CH3:10])[N:12]=1)[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 819233,5-HeptanedioneHCID 27748831-Mesitylhydrazine hydrochloride

Product 1

HCID 218373383,5-Diethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazoleYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7.46 g (0.04 mol) of 2,4,6-trimethylphenylhydrazine hydrochloride, 5.12 g (0.40 mol) of 3,5-heptanedione and 4.18 mL (0.60 mol) of triethylamine in 100 mL of absolute ethanol was refluxed overnight. The solvent was evaporated from the cooled reaction mixture and the residues were partitioned between water and ethyl acetate. The organic extracts were dried with brine and magnesium sulfate, and the solvent was evaporated to give the desired product in 95% yield. This compound was used in the subsequent reaction without further purification 1H-NMR (CDCl3): 11 (3H, t, J=7),1.24 (3H, t, J=7),1.90 (6H, s), 2.22 (2H, q, J-7), 2.28 (3H, 5.96 (1H, s), 6.86 (2H, s).

Workup

  1. customThe solvent was evaporated from the cooled reaction mixture
  2. customthe residues were partitioned between water and ethyl acetate
  3. dry with materialThe organic extracts were dried with brine and magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-501cfd35dfe5428f9ac1bef1d7ccdcef
Source dataset
uspto-grants-1999_10
Patent number
US05968944

Reaction notes

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