Dimethylformamide → 1-(m-nitrophenyl)-3-methylquinazoline-2,4(1H, 3H)-dione

HRID 328120

Reaction equation

HRID 328120 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].[CH3:22]N(C)C=O.[H-].[Na+].S(OC)(OC)=O>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]([CH3:22])[C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 69223Dimethyl sulfiteHCID 128123771-(m-nitrophenyl)quinazoline-2,4(1H, 3H)-dione

Product 1

HCID 128123781-(m-nitrophenyl)-3-methylquinazoline-2,4(1H, 3H)-dione

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 0.6 g of approximately 55 % sodium hydride, and the solution was stirred for 20 minutes at room temperature. To this was added 2.2 g of dimethyl sulfite and stirring was further continued for 4 hours at room temperature. After the reaction was complete, the solvent was removed from the reaction mixture by distillation under reduced pressure. The residue thus obtained was mixed with water to precipitate a crude product. This product was recrystallized from methanol to afford 2.8 g of 1-(m-nitrophenyl)-3-methylquinazoline-2,4(1H, 3H)-dione as colorless needles, melting at 242°-243° C.

Workup

  1. stirringstirring
  2. waitwas further continued for 4 hours at room temperature
  3. customthe solvent was removed from the reaction mixture by distillation under reduced pressure
  4. customThe residue thus obtained
  5. customto precipitate a crude product
  6. customThis product was recrystallized from methanol

Sources & evidence

ORD record
ord-0c4cbc72e24d4188a445601834301607
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Linked notes

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