Sodium hydride → HCID 19092249, compound

HRID 487580Notes

Reaction equation

HRID 487580 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]([OH:15])[CH3:14])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].Cl[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][N:18]=1>CN(C=O)C>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([CH:13]([O:15][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH3:14])=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 788644-ChloroquinazolineHCID 2607311-(4-tert-Butylphenyl)ethanol

Product 1

HCID 19092249HCID 19092249, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 0.5 g of sodium hydride in 100 ml of DMF was added 2.0 g of 1-[4-(t-butyl)phenyl]ethanol, and the resulting mixture was stirred at room temperature for one hour. Then 1.8 g of 4-chloroquinazoline in 30 ml of DMF were added. The mixture was stirred at room temperature for three hours, then poured into an ice/water mixture. The product was extracted into ether, the ether solution was concentrated and the residue was recrystallized from a pentane/ethyl acetate mixture to give 0.300 g of the title product. M.P. 85°-86° C.

Workup

  1. stirringThe mixture was stirred at room temperature for three hours
  2. extractionThe product was extracted into ether
  3. concentrationthe ether solution was concentrated
  4. customthe residue was recrystallized from a pentane/ethyl acetate mixture

Sources & evidence

ORD record
ord-c75eacdf37bd492aa31cecad1b55693d
Source dataset
uspto-grants-1994_03
Patent number
US05296484

Reaction notes

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