Sodium hydride → HCID 18919046, compound

HRID 1291328Notes

Reaction equation

HRID 1291328 reaction equation
[Cl: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>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:15]=[CH:14][C:11]([CH2:12][O:13][C:21]3[N:30]([CH3:31])[C:29](=[O:32])[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][C:27]=4[CH3:33])[N:22]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 18919228HCID 18919228, compoundHCID 19689351HCID 19689351, compound

Product 1

HCID 18919046HCID 18919046, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-chlorobenzoyl)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 (850 mg) was added and the mixture was stirred at room temperature for 1 hour and at 80° C. for 10 minutes. 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: chloroform=4:1:1) to provide the title compound as colorless solid (350 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour and at 80° C. for 10 minutes
  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: chloroform=4:1:1)

Sources & evidence

ORD record
ord-d51f8c5670fb402a8a3bbbc265d6281d
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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