Benzene, 1-chloro-3-isocyanato- → 1(m-nitrophenyl)-3-allylquinazoline-2,4(1H, 3H)-dione

HRID 328131

Reaktionsgleichung

Reaktionsgleichung von HRID 328131
[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].[H-].[Na+].ClC1C=C(N=[C:33]=[O:34])C=CC=1>O1CCCC1>[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:33]2=[O:34])[CH:20]=[CH:21][CH:22]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 24758Sodium hydrideHCID 214440042-(m-nitroanilino)-N-allylbenzamide

Produkt 1

HCID 132723441(m-nitrophenyl)-3-allylquinazoline-2,4(1H, 3H)-dioneAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3.0 g of 2-(m-nitroanilino)-N-allylbenzamide was dissolved in 20 ml of tetrahydrofuran. To the solution was added 1.0 g of approximately 50 % sodium hydride and stirring was performed for 30 minutes. To this was added dropwise under cooling 4.6 g of m-chlorophenyl isocyanate, and the mixture was stirred for one hour, and then refluxed for 5 hours. After the reaction was complete, the solvent was distilled off from the resulting mixture. The residue thus obtained was recrystallized from methanol to give 2.3 g of 1-(m-nitrophenyl)-3-allylquinazoline-2,4(1H, 3H)-dione as colorless needles, melting at 165°-166° C.

Aufarbeitung

  1. additionTo this was added dropwise
  2. stirringthe mixture was stirred for one hour
  3. temperaturerefluxed for 5 hours
  4. distillationthe solvent was distilled off from the resulting mixture
  5. customThe residue thus obtained
  6. customwas recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-519dbbb3c2ea4057b55b69026901ce1e
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04016166

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