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

HRID 328122Notes

Reaction equation

HRID 328122 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.[O-]CC.[Na+].[CH:31]1([CH2:34]Br)[CH2:33][CH2:32]1>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]([CH2:34][CH:31]3[CH2:33][CH2:32]3)[C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81503BromomethylcyclopropaneHCID 2723922Sodium ethoxideHCID 128123771-(m-nitrophenyl)quinazoline-2,4(1H, 3H)-dione

Product 1

HCID 132723431-(m-nitrophenyl)-3-cyclopropylmethyl-quinazoline-2,4(1H, 3H)-dioneYield 93%

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 1.4 g of sodium ethoxide, and the whole was stirred for 30 minutes at room temperature. To this was further added 4.1 g of cyclopropylmethyl 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. Recrystallization of this product from methanol gave 3.1 g of 1-(m-nitrophenyl)-3-cyclopropylmethyl-quinazoline- 2,4(1H, 3H)-dione as colorless needles, melting, at 163°-164° 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. customRecrystallization of this product from methanol

Sources & evidence

ORD record
ord-9e39a75442664cf3af4ce58005669c45
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

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