Sodium hydride → 1-methyl-4-(4-methylphenyl)-3-(2-phenoxyethoxy)-1H-pyrazol-5-amine

HRID 1062778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062778
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([OH:8])[C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.[H-].[Na+].Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][CH3:27]>CN(C)C=O.O>[CH3:7][N:6]1[C:2]([NH2:1])=[C:3]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[C:4]([O:8][CH2:27][CH2:26][O:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:19]=2)=[N:5]1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 685002-BromophenetoleHCID 1784239155-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-ol

Produkt 1

HCID 222820241-methyl-4-(4-methylphenyl)-3-(2-phenoxyethoxy)-1H-pyrazol-5-amineAusbeute 25,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-ol (Preparation 3a) (50 mg) in dimethylformamide (2 ml) at room temperature was added sodium hydride (60% dispersion in oil, 10 mg) and bromophenetole (49.5 mg). The mixture was stirred for 2 hrs. The reaction was diluted with water (10 ml) and extracted with ethyl acetate (10 ml). The organic fraction was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (10 g) eluted with ether to yield the title compound as a white solid (20 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate (10 ml)
  2. dry with materialThe organic fraction was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica (10 g)
  6. washeluted with ether

Quellen und Nachweise

ORD-Eintrag
ord-0d6f0465b82242d285f0cbcce972f264
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962923B2

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