4-Amino-2,6-dimethylphenol → 2,6-dimethyl-4-[(2-phenyl-3,4-dihydropyrazol-5-yl)amino]phenol

HRID 22274

Reaktionsgleichung

Reaktionsgleichung von HRID 22274
[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[C:11]1([N:17]2[CH2:21][CH2:20][C:19](N)=[N:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:11]1([N:17]2[CH2:21][CH2:20][C:19]([NH:8][C:6]3[CH:7]=[C:2]([CH3:1])[C:3]([OH:10])=[C:4]([CH3:9])[CH:5]=3)=[N:18]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

5

Edukt 2

HCID 826684-Amino-2,6-dimethylphenolHCID 987363-Amino-1-phenylpyrazole

Produkt 1

HCID 1784283642,6-dimethyl-4-[(2-phenyl-3,4-dihydropyrazol-5-yl)amino]phenolAusbeute 46,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2,6-dimethyl-4-aminophenol (15 g) and 4,5-dihydro-1-phenyl-1H-pyrazol-3-amine (17.6 g) were heated with p-toluene sulfonic acid (0.2 g) at 160° for 1 hour under nitrogen. The mix was cooled, taken up in dichloromethane and washed with dilute HCl, and water. Evaporation, and chromatography of the residue (silica, dichloromethane/ethyl acetate [9:1]) gave 4-(4,5-dihydro-1-phenyl-1H-pyrazol-3-yl)amino-2,6-dimethylphenol (14.2 g), mp 154°-158°. This was refluxed in toluene (40 ml) with 10% palladium on charcoal (10 g) for 3 hours. The mixture was filtered and evaporated to give, after crystallisation from cyclohexane/ethyl acetate, the title compound (8 g), mp 154°-155°.

Aufarbeitung

  1. temperatureThe mix was cooled
  2. washwashed with dilute HCl, and water
  3. customEvaporation, and chromatography of the residue (silica, dichloromethane/ethyl acetate [9:1])

Quellen und Nachweise

ORD-Eintrag
ord-588e7610c0864434bdfdba69889f02e0
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428044

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