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

HRID 328119Notes

Reaction equation

HRID 328119 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(F)(OC)(=O)=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 9870Methyl fluorosulfateHCID 24758Sodium hydrideHCID 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 30 minutes at room temperature. To this was added 2.3 g of methyl fluorosulfate, and the whole was reacted for one hour at room temperature. After the reaction was complete, the solvent was distilled off from the reaction mixture under reduced pressure. To the residue obtained was added water to precipitate a crude product. Recrystallization of this product from methanol gave 2.7 g of 1-(m-nitrophenyl)- 3-methylquinazoline-2,4(1H, 3H)-dione as colorless needles, melting at 241°-242° C.

Workup

  1. customthe whole was reacted for one hour at room temperature
  2. distillationthe solvent was distilled off from the reaction mixture under reduced pressure
  3. customTo the residue obtained
  4. customto precipitate a crude product
  5. customRecrystallization of this product from methanol

Sources & evidence

ORD record
ord-aa3834151ddd49579c0cbd12f23301b3
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

Loading…