Triethylamine → N-(5-hydroxy-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874330Notes

Reaction equation

HRID 1874330 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].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>O1CCCC1.O>[OH:9][C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[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:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 178203-Amino-p-cresolHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chloride

Product 1

HCID 57505436N-(5-hydroxy-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 63.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-amino-4-methylphenol (3.71 g, 30.1 mmol) and triethylamine (4.38 mL, 31.6 mmol) in tetrahydrofuran (30 mL) was added dropwise with stirring under ice-cooling a solution of 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (5.02 g, 31.6 mmol) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was collected by filtration and washed with ethyl acetate-hexane to give the title compound (4.67 g, 63%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 hr
  2. extractionextracted with ethyl acetate (×3)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. filtrationthe residue was collected by filtration
  8. washwashed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-fcbd8c45b1ad4d24942f2f4f54d4f25a
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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