Sodium hydride → Fenazaquin

HRID 35836

Reaction equation

HRID 35836 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[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.O>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][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)=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 788644-ChloroquinazolineHCID 79410p-tert-Butylphenethyl alcohol

Product 1

HCID 86356FenazaquinYield 28.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1.1 g of sodium hydride in 50 ml of DMF, 4.0 g of 2-[4-(t-butyl)phenyl]ethanol was added, 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 at room temperature overnight. The mixture was then poured into a mixture of ice in water. The product was extracted into CH2Cl2, and the resulting solution was concentrated to dryness. TLC showed one major spot and five minor spots. The product was purified by HPLC (silica gel, CH2Cl2). The fractions containing the major product were collected and concentrated, giving 1.9 g of the title product. Yield: 28.4%. M.P. 70°-71° C.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionThe product was extracted into CH2Cl2
  3. concentrationthe resulting solution was concentrated to dryness
  4. customThe product was purified by HPLC (silica gel, CH2Cl2)
  5. additionThe fractions containing the major product
  6. customwere collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-378409998bb94c5480b3bbf142ebb392
Source dataset
uspto-grants-1995_05
Patent number
US05411963

Linked notes

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