Water → HCID 13207875, compound

HRID 918248Notes

Reaction equation

HRID 918248 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[NH:10][C:9](=[O:20])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:24][CH:25]1[CH2:30][CH:29]2[CH2:31][CH:26]1[CH2:27][CH2:28]2.O>CN(C)C=O>[CH:26]12[CH2:31][CH:29]([CH2:28][CH2:27]1)[CH2:30][CH:25]2[CH2:24][N:10]1[C:11]2[C:16](=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][C:9]1=[O:20].[CH:26]12[CH2:31][CH:29]([CH2:28][CH2:27]1)[CH2:30][CH:25]2[CH2:24][O:20][C:9]1[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=2)[N:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 613149HCID 613149, compoundHCID 1262565355932-58-6

Product 2

HCID 13207875HCID 13207875, compoundHCID 21521519HCID 21521519, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 11 g of 4-phenyl-6-nitro-2(1H)-quinazolinone in 100 ml of dimethylformamide, was added 2.2 g of 52.9% sodium hydride. After stirring at 50°C for 1 hour, 17 g of 2-bromomethyl norbornane was added and the reaction mixture was heated under reflux for 8 hours. After cooling, the mixture was poured into 1l of water and the resulting mixture was extracted with chloroform. The chloroform layer was washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residual oil was chromatographed on silica gel using chloroform as eluting solvent to obtain 1-(2-norbornylmethyl)-4-phenyl-6-nitro-2(1H)-quinazolinone and 2-(2-norbornylmethoxy)-4-phenyl-6-nitroquinazoline. The former was recrystallized from a mixture of carbon tetrachloride and diethyl ether, to give yellow needles, m.p. 160°- 161°C, and the latter was recrystallized from methylchloroform, to give yellow needles, m.p. 153°- 155°C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 8 hours
  3. temperatureAfter cooling
  4. extractionthe resulting mixture was extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customThe residual oil was chromatographed on silica gel
  9. washas eluting solvent

Sources & evidence

ORD record
ord-a0816b5404e84f03938bd8b58126f215
Source dataset
uspto-grants-1976_07
Patent number
US03970654

Reaction notes

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