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

HRID 328125

Reaktionsgleichung

Reaktionsgleichung von HRID 328125
[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[NH:7][C:8]1[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=1[C:10]([NH:12][CH2:13][CH:14]=[CH2:15])=[O:11])([O-:3])=[O:2].[O:23]1CCC[CH2:24]1.[H-].[Na+].C(Cl)(Cl)=O.C1(C)C=CC=CC=1>O>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[C:8]3[C:9](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:10](=[O:11])[N:12]([CH2:13][CH:14]=[CH2:15])[C:24]2=[O:23])[CH:20]=[CH:21][CH:22]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 19083224Phosgen tolueneHCID 214440042-(m-nitroanilino)-N-allylbenzamide

Produkt 1

HCID 132723441(m-nitrophenyl)-3-allylquinazoline-2,4(1H, 3H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 3.0 g of 2-(m-nitroanilino)-N-allylbenzamide and 25 ml of tetrahydrofuran was added 1.1 g of 50 % sodium hydride, and the whole was stirred for 30 minutes at room temperature. To this was added dropwise under cooling 16 g of 30 % phosgene-toluene solution, and the mixture was stirred for one hour at room temperature and then refluxed for 2 hours. After the reaction was finished, the solvent was distilled off from the resulting mixture, and to the residue obtained was added water to precipitate a crude product. This product was recrystallized from methanol to yield 2.8 g of 1-(m-nitrophenyl)-3-allylquinazoline-2,4(1H, 3H)-dione as colorless needles, melting at 164°-166° C.

Aufarbeitung

  1. additionTo this was added dropwise
  2. stirringthe mixture was stirred for one hour at room temperature
  3. temperaturerefluxed for 2 hours
  4. distillationthe solvent was distilled off from the resulting mixture
  5. customto the residue obtained
  6. customto precipitate a crude product
  7. customThis product was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-275e0f4243df42678651f6d289c93cb3
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04016166

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