Sodium hydride → HCID 18919023, compound

HRID 1291329Notes

Reaction equation

HRID 1291329 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:21]1[N:30]([CH3:31])[C:29](=[O:32])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[CH3:33])[N:22]=1>CN(C=O)C>[CH3:31][N:30]1[C:29](=[O:32])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[CH3:33])[N:22]=[C:21]1[O:13][CH2:12][C:11]1[CH:14]=[CH:15][C:8]([C:6](=[O:7])[C:5]2[CH:16]=[CH:17][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 18919228HCID 18919228, compoundHCID 54483725HCID 54483725, compound

Product 1

HCID 18919023HCID 18919023, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-fluorobenzoyl)benzyl alcohol (1.0 g) in DMF (20 ml) was added 60% sodium hydride (210 mg) and the mixture was stirred at room temperature for 10 minutes. Then, 2-chloro-3,5-dimethyl-4(3H)-quinazolinone (907 mg) was added and the mixture was stirred at room temperature for 1 hour. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate =3:1) to provide the title compound as colorless solid (560 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. concentrationThis reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate =3:1)

Sources & evidence

ORD record
ord-e77f7b9296e641b98714035274969546
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…