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

HRID 725276Notes

Reaction equation

HRID 725276 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): 0.11 (3H, t, J=7), 1.24 (3H, t, J=7), 1.90 (6H, s), 2.22 (2H, q, J-7), 2.28 (3H, s), 2.65 ) (2H, q, J=7), 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-2886b1c7caa94998bbaa10383f0b9411
Source dataset
uspto-grants-1998_01
Patent number
US05705646

Reaction notes

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