Dimethylformamide → Nitraquazone

HRID 328117Notes

Reaction equation

HRID 328117 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[NH:12][C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CN(C)C=O.[H-].[Na+].[CH2:29](I)[CH3:30]>O>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[N:12]([CH2:29][CH3:30])[C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 128123771-(m-nitrophenyl)quinazoline-2,4(1H, 3H)-dione

Product 1

HCID 68765NitraquazoneYield 87.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.8 g of 1-(m-nitrophenyl)quinazoline-2,4(1H, 3H)-dione and 30 ml of dimethylformamide was added 0.5 g of approximately 55 % sodium hydride, and the solution was stirred for 30 minutes. To this was further added 4.7 g of ethyl iodide and stirring was further continued for 1.5 hours at room temperature. After the reaction was complete, the solvent was distilled off from the mixture under reduced pressure. To the residue obtained was added water to precipitate a crude product, which was then recrystallized from methanol to give 2.7 g of 1-(m-nitrophenyl)-3-ethylquinazoline-2,4 (1H, 3H)-dione as light brown prisms, melting at 193°-194° C.

Workup

  1. stirringstirring
  2. waitwas further continued for 1.5 hours at room temperature
  3. distillationthe solvent was distilled off from the mixture under reduced pressure
  4. customTo the residue obtained
  5. customto precipitate a crude product, which
  6. customwas then recrystallized from methanol

Sources & evidence

ORD record
ord-50c2225b0c7e445f8f81ed155e3c1f30
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

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