Tetrahydrofuran → Nitraquazone

HRID 328123Notes

Reaction equation

HRID 328123 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].O1CC[CH2:24][CH2:23]1.C(OC(OCC)N(C)C)C>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]([CH2:23][CH3:24])[C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 70913Dimethylformamide diethylacetalHCID 128123771-(m-nitrophenyl)quinazoline-2,4(1H, 3H)-dione

Product 1

HCID 68765Nitraquazone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.8 g of 1-(m-nitrophenyl)quinazoline-2,4(1H, 3H)-dione, 40 ml of dry tetrahydrofuran and 4.4 g of N,N-dimethylformamide diethyl acetal was refluxed for 6 hours. 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, which was then recrystallized from methanol to produce 2.8 g of 1-(m-nitrophenyl)- 3-ethylquinazoline-2,4(1H, 3H)-dione as colorless prisms, melting at 193°-194° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. distillationthe solvent was distilled off from the reaction mixture under reduced pressure
  3. customTo the residue obtained
  4. customto precipitate a crude product, which
  5. customwas then recrystallized from methanol

Sources & evidence

ORD record
ord-98d4c0711cd64ff2a02d07e1d64b5170
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

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