Triethylamine → 3-(tert-Butyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amine

HRID 16951

Reaktionsgleichung

Reaktionsgleichung von HRID 16951
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:19]([CH2:25][C:26]#[N:27])(=O)[C:20]([CH3:23])([CH3:22])[CH3:21]>C1(C)C=CC=CC=1>[C:20]([C:19]1[CH:25]=[C:26]([NH2:27])[N:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[N:11]=1)([CH3:23])([CH3:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 27239044-Methoxyphenylhydrazine hydrochloride

Produkt 1

HCID 111393953-(tert-Butyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amineAusbeute 70,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Solid 4-methoxyphenylhydrazine hydrochloride (25.3 g) was suspended in toluene (100 mL) and treated with triethylamine (20.2 g). The mixture was stirred at RT for 30 min and treated with pivaloylacetonitrile (18 g). The reaction was heated to reflux and stirred overnight. The hot mixture was filtered, the solids washed with hexane and dried in vacuo to afford 3-tert-butyl-1-(4-methoxyphenyl)-1H-pyrazol-5-amine (25 g, 70%). 1H NMR (DMSO-d6): δ 7.5 (d, 2H), 7.0 (d, 1H), 6.4 (s, 11H), 6.1 (s, 2H), 3.9 (s, 34H), 1.3 (s, 9H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. stirringstirred overnight
  4. filtrationThe hot mixture was filtered
  5. washthe solids washed with hexane
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-160afc0f93df47d2aca1036e5581711e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737283B2

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