Water → 6-Nitro-4-(2-(4-tert-butylphenyl)ethoxy)quinazoline

HRID 1392882

Reaktionsgleichung

Reaktionsgleichung von HRID 1392882
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][OH:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[N+:16]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[CH:24][N:23]=[C:22]2Cl)([O-:18])=[O:17].O>O1CCCC1>[N+:16]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[CH:24][N:23]=[C:22]2[O:13][CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)([O-:18])=[O:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79410p-tert-Butylphenethyl alcoholHCID 113562574-Chloro-6-nitroquinazoline

Produkt 1

HCID 596786596-Nitro-4-(2-(4-tert-butylphenyl)ethoxy)quinazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-(4-tert-butylphenyl) ethanol (1.0 g, 5.59 mmol) is dissolved in dry tetrahydrofuran (7 ml) and to it is added sodium hydride (48.5 mg, 2.02 mmol). The resulting solution is stirred at room temperature for 30 minutes after which 6-Nitro-4-chloroquinazoline (1.17 g, 5.6 mmol) is added to the above solution. The solution is then stirred for 6 hours after which water is added to the mixture. The solution is then extracted in dichloromethane. The organic layer is washed, dried and then concentrated to yield the crude product which is purified by flash chromatography (silica gel; ethyl acetate/hexanes) to give the product.

Aufarbeitung

  1. additionis added to the above solution
  2. additionis added to the mixture
  3. extractionThe solution is then extracted in dichloromethane
  4. washThe organic layer is washed
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-18ff397e46024000b0cb299cd15e00bd
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07344702B2

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