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

HRID 328118Notes

Reaction equation

HRID 328118 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](Br)[CH:30]=[CH2:31]>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]([CH2:31][CH:30]=[CH2:29])[C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 128123771-(m-nitrophenyl)quinazoline-2,4(1H, 3H)-dione

Product 1

HCID 132723441(m-nitrophenyl)-3-allylquinazoline-2,4(1H, 3H)-dioneYield 90.7%

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 0.6 g of approximately 55 % sodium hydride and the solution was stirred for 30 minutes at room temperature. To this was further added 3.6 g of allyl bromide, and the mixture was reacted for 2 hours at room temperature. Then, the solvent was distilled off from the resulting mixture under reduced pressure to leave a residue, to which was added water to precipitate a crude product. This product was recrystallized from methanol to yield 2.9 g of 1(m-nitrophenyl)-3 -allylquinazoline- 2,4(1H, 3H)-dione as light brown needles, melting at 165°-166° C.

Workup

  1. customthe mixture was reacted for 2 hours at room temperature
  2. distillationThen, the solvent was distilled off from the resulting mixture under reduced pressure
  3. customto leave a residue
  4. customto precipitate a crude product
  5. customThis product was recrystallized from methanol

Sources & evidence

ORD record
ord-c0bfb59fdce74feeaef789a5fb0ed9a2
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

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