Sodium hydride → Quinazoline, 4-(2-(4-chlorophenyl)ethoxy)-

HRID 35838

Reaction equation

HRID 35838 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1.Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][N:15]=1>CN(C=O)C.O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][N:15]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74647p-Chlorophenethylic alcoholHCID 788644-Chloroquinazoline

Product 1

HCID 164154Quinazoline, 4-(2-(4-chlorophenyl)ethoxy)-Yield 2.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1.1 g of sodium hydride in 50 ml of DMF was added 3.4 g of 2-(4-chlorophenyl)ethanol, and the mixture was stirred at room temperature for one hour. Then 3.6 g of 4-chloroquinazoline in 20 ml of DMF were added, and the mixture was stirred overnight. The mixture was then poured into a mixture of ice in water. Solid was collected and recrystallized from pentane giving 0.149 g of the title product. Yield: 2.4%. M.P. 57°-58° C.

Workup

  1. stirringthe mixture was stirred overnight
  2. customSolid was collected
  3. customrecrystallized from pentane giving 0.149 g of the title product

Sources & evidence

ORD record
ord-ca27611c751f4bdab9cd7b26cf35749a
Source dataset
uspto-grants-1995_05
Patent number
US05411963

Linked notes

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