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

HRID 328121Notes

Reaction equation

HRID 328121 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.P(OC)(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

5

Reactant 3

HCID 6228DimethylformamideHCID 10541Trimethyl PhosphateHCID 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 20 ml of dimethylformamide was added 4.2 g of trimethyl phosphate and the whole was refluxed for 5 hours. After the reaction was complete, the solvent was distilled off from the reaction mixture under reduced pressure. To the residue thus obtained was added water to precipitate a crude product. This product was recrystallized from methanol to yield 2.4 g of 1-(m-nitrophenyl)-3-methylquinazoline-2,4(1H, 3H)-dione as colorless needles, melting at 241°-242° C.

Workup

  1. temperaturethe whole was refluxed for 5 hours
  2. distillationthe solvent was distilled off from the reaction mixture under reduced pressure
  3. customTo the residue thus obtained
  4. customto precipitate a crude product
  5. customThis product was recrystallized from methanol

Sources & evidence

ORD record
ord-2f7de6e27c284eceb1939061b2c42622
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

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