Triethylamine → N-(2-fluoro-5-hydroxyphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874339Notes

Reaction equation

HRID 1874339 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F: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>[F:8][C:7]1[CH:6]=[CH:5][C:4]([OH:9])=[CH:3][C:2]=1[NH:1][C:23]([C:22]1[N:18]([CH3:17])[N:19]=[C:20]([CH3:26])[CH:21]=1)=[O:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 135191803-Amino-4-fluorophenol

Product 1

HCID 57505434N-(2-fluoro-5-hydroxyphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-amino-4-fluorophenol (5.05 g, 39.7 mmol) and triethylamine (5.77 mL, 41.7 mmol) in tetrahydrofuran (30 mL) was added dropwise with stirring under ice-cooling a solution of 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (6.61 g, 41.7 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 (9.89 g, 99%) 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-b046997bf2234390b8a9b630c74bfc36
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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