Sodium Hydroxide → 3-(4,4'-dimethoxybenzhydryl)-2-propyl-6-nitroquinazolin-4(3H)-one

HRID 37229Notes

Reaction equation

HRID 37229 reaction equation
[H-].[Na+].[CH2:3]([C:6]1[NH:7][C:8]2[C:13]([C:14](=[O:16])[N:15]=1)=[CH:12][C:11]([N+:17]([O-:19])=[O:18])=[CH:10][CH:9]=2)[CH2:4][CH3:5].[H][H].[CH3:22][O:23][C:24]1[CH:39]=[CH:38][C:27]([CH:28](Cl)[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[CH:26][CH:25]=1.[OH-].[Na+]>CN(C=O)C>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([CH:28]([N:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=3)[N:7]=[C:6]2[CH2:3][CH2:4][CH3:5])[C:27]2[CH:38]=[CH:39][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)=[CH:34][CH:33]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 10706646bis(4-methoxyphenyl)chloromethaneHCID 178418361HCID 178418361, compoundHCID 178440202HCID 178440202, compound

Product 1

HCID 200766253-(4,4'-dimethoxybenzhydryl)-2-propyl-6-nitroquinazolin-4(3H)-oneYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 1.01 g (33.7 mmol) of 80% sodium hydride in 20 mL of dry DMF was added at 0° C. 7.5 g (32 mmol) of the product of Step A as a solid. The reaction mixture was diluted with a further 50 mL of DMF to assist stirring. After hydrogen evolution was complete, a solution of 8.8 g (33.7 mmol) of 4,4'-dimethoxybenzhydryl chloride in 20 mL of dry DMF was added dropwise. The reaction mixture was stirred overnight and then poured into 300 mL of 0.1N NaOH. The precipitate was collected by filtration and dried under vacuum to give 12.1 g (94%) of a yellow solid.

Workup

  1. additionwas added at 0° C
  2. stirringThe reaction mixture was stirred overnight
  3. filtrationThe precipitate was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c8bc872258e946af8506212c353f07c0
Source dataset
uspto-grants-1995_05
Patent number
US05420133

Reaction notes

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