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

HRID 1874343

Reaktionsgleichung

Reaktionsgleichung von HRID 1874343
[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

Komponenten

8

Edukt 4

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

Produkt 1

HCID 57749292N-(3-hydroxy-5-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamideAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-196f89d502e34c79899fc4d935afacae
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

Verknüpfte Notizen

Wird geladen…