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

HRID 35842

Reaction equation

HRID 35842 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 180255Quinazoline, 4-(2-(1,1'-biphenyl)-4-ylethoxy)-Yield 30.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7bb7da0e0d064691b38524fa0f9a41fd
Source dataset
uspto-grants-1995_05
Patent number
US05411963

Linked notes

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