Sodium hydride → Quinazoline, 4-(2-(1,1'-biphenyl)-4-ylethoxy)-

HRID 35842

Reaktionsgleichung

Reaktionsgleichung von HRID 35842
[H-].[Na+].[C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.Cl[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=[CH:21][N:20]=1>CN(C=O)C.O>[C:3]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[CH:21][N:20]=2)=[CH:7][CH:8]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 788644-ChloroquinazolineHCID 64245772-[1,1'-Biphenyl]-4-yl-1-ethanol

Produkt 1

HCID 180255Quinazoline, 4-(2-(1,1'-biphenyl)-4-ylethoxy)-Ausbeute 30,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 0.53 g of sodium hydride in 200 ml of DMF was added 2.2 g of 2-[(1,1'-biphenyl)-4-yl]ethanol, and the mixture was stirred at room temperature for one hour. Then 1.8 g of 4-chloroquinazoline in 20 ml of DMF were added, and the mixture was stirred at room temperature for another three hours. The mixture was then poured into a mixture of ice in water. The solid phase was collected and washed with water. TLC showed two spots. The product was purified using HPLC (silica gel, CH2Cl2) giving 1.1 g of the title product. Yield: 30.6%. M.P. 72°-74° C.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for another three hours
  2. customThe solid phase was collected
  3. washwashed with water
  4. customThe product was purified

Quellen und Nachweise

ORD-Eintrag
ord-7bb7da0e0d064691b38524fa0f9a41fd
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411963

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