Triethylamine → N-(3-hydroxy-5-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874343

Reaction equation

HRID 1874343 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(N(CC)CC)C.[CH3:17][N:18]1[C:22]([C:23](Cl)=[O:24])=[CH:21][C:20]([CH3:26])=[N:19]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.CO>[OH:9][C:4]1[CH:3]=[C:2]([NH:1][C:23]([C:22]2[N:18]([CH3:17])[N:19]=[C:20]([CH3:26])[CH:21]=2)=[O:24])[CH:7]=[C:6]([CH3:8])[CH:5]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 30186673-Amino-5-methylphenol

Product 1

HCID 57749292N-(3-hydroxy-5-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 96.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-amino-5-methylphenol (4.32 g, 35.1 mmol) and triethylamine (5.20 mL, 37.4 mmol) in tetrahydrofuran (40 mL) was added dropwise with stirring under ice-cooling a solution of 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (5.85 g, 36.9 mmol) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 10 hr. Methanol (40 mL), water (40 mL) and saturated aqueous sodium carbonate solution (20 mL) were added to the reaction mixture, and the mixture was stirred at room temperature for 7 hr. The reaction solution was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=100/0→50/50) to give the title compound (8.30 g, 96%) as a pale-yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 hr
  2. stirringthe mixture was stirred at room temperature for 7 hr
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionEthyl acetate was added to the residue
  5. washthe mixture was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltrated
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=100/0→50/50)

Sources & evidence

ORD record
ord-196f89d502e34c79899fc4d935afacae
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Linked notes

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