Methyl iodide → 6-chloro-1-methyl-4-phenyl-2(1H)quinazolinone 3-oxide

HRID 971463Notes

Reaction equation

HRID 971463 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N+:6]([O-:13])=[C:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Na+].[CH3:22]I>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:22])[C:7](=[O:12])[N+:6]([O-:13])=[C:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178518621HCID 178518621, compound

Product 1

HCID 234716266-chloro-1-methyl-4-phenyl-2(1H)quinazolinone 3-oxideYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5 g (0.018 mole) of 6-chloro-4-phenyl-2(1H)quinazolinone 3-oxide and 125 ml of N,N-dimethylformamide was added, at room temperature, 0.96 g of sodium hydride (50% in oil). The temperature rose to 30° and the stirring was continued for approximately 30 minutes to effect salt formation To this mixture was added, dropwise, 6 g (0.042 mole) of methyl iodide. Stirring was continued for approximately 2 hours and the solid was collected by filtration, washed with water and with 10 ml of 1N HCl to give 3.98 g (78%) of product identified as 6-chloro-1-methyl-4-phenyl-2(1H)-quinazoline 3-Oxide: mp 253°-254°. 1H nmr (CF3CO2H) δ 3.12 ppm (s, 3H); δ 6.5-7.3 (m, 8H, aromatic).

Workup

  1. additionwas added, at room temperature
  2. customrose to 30°
  3. additionwas added
  4. waitwas continued for approximately 2 hours
  5. filtrationthe solid was collected by filtration
  6. washwashed with water and with 10 ml of 1N HCl

Sources & evidence

ORD record
ord-cc94d6c1eab14d38bd55556bf6105202
Source dataset
uspto-grants-1979_07
Patent number
US04160092

Reaction notes

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