Sodium hydride → 8-Fluoro-4-[2-(4-methylphenyl)ethoxy]quinazoline

HRID 35844

Reaction equation

HRID 35844 reaction equation
[H-].[Na+].Cl[C:4]1[C:13]2[C:8](=[C:9]([F:14])[CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][N:5]=1.[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][OH:24])=[CH:18][CH:17]=1>CN(C=O)C>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[N:7]=[CH:6][N:5]=[C:4]2[O:24][CH2:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 952944-Methylphenethyl alcoholHCID 199391334-Chloro-8-fluoroquinazoline

Product 1

HCID 199390858-Fluoro-4-[2-(4-methylphenyl)ethoxy]quinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.6 g of sodium hydride (50%, suspension in oil) and 2 g of 4-chloro-8-fluoroquinazoline in 20 ml of DMF was added 1.64 g of 2-(4-methylphenyl)ethanol, and the mixture was stirred for one hour. Then the mixture was poured into ice water. The solid was collected by filtration. Yield: 0.7 g (20.5%). M.P. 72°-74° C.

Workup

  1. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-25910daf5c584d5dabadded8b8a7a749
Source dataset
uspto-grants-1995_05
Patent number
US05411963

Linked notes

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