Tetrahydrofuran → Nitraquazone

HRID 328124Notes

Reaction equation

HRID 328124 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[NH:7][C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[C:10]([NH:12][CH2:13][CH3:14])=[O:11])([O-:3])=[O:2].[O:22]1CCC[CH2:23]1.[H-].[Na+].C(Cl)(=O)OCC>O>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[C:8]3[C:9](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:10](=[O:11])[N:12]([CH2:13][CH3:14])[C:23]2=[O:22])[CH:19]=[CH:20][CH:21]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 133056782-(m-nitroanilino)-N-ethylbenzamide

Product 1

HCID 68765Nitraquazone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.9 g of 2-(m-nitroanilino)-N-ethylbenzamide and 25 ml of tetrahydrofuran was added 1.0 g of 50 % sodium hydride, and stirring was performed for 30 minutes at room temperature. To this was added dropwise under cooling 5.4 g of ethyl chlorocarbonate, and the mixture was allowed to stand for one hour at room temperature and then refluxed for 10 hours. After the reaction was complete, the solvent was evaporated from the reaction mixture under reduced pressure, and to the residue obtained was added water to prepicpitate a crude product. This product was recrystallized from methanol to give 2.5 g of 1-(m-nitrophenyl)-3-ethylquinazoline-2,4(1H, 3H)-dione as colorless prisms, melting at 193°-194° C.

Workup

  1. additionTo this was added dropwise
  2. waitto stand for one hour at room temperature
  3. temperaturerefluxed for 10 hours
  4. customthe solvent was evaporated from the reaction mixture under reduced pressure
  5. customto the residue obtained
  6. customThis product was recrystallized from methanol

Sources & evidence

ORD record
ord-0cf5d302d5a14ad78d22f3d4b362dcfb
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

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