Aniline → 3-Phenylquinazolinone

HRID 511779

Reaktionsgleichung

Reaktionsgleichung von HRID 511779
C[C:2]1[O:3][C:4](=O)[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1([N:13]2[CH:4]=[C:5]3[C:6]([CH:8]=[CH:9][CH:10]=[CH:11]3)=[N:7][C:2]2=[O:3])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

3

Edukt 2

HCID 6115AnilineHCID 68236Acetanthranil

Produkt 1

HCID 671201143-PhenylquinazolinoneAusbeute 35,2 %

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 2-methyl-4H-Benzo[d][1,3]oxazin-4-one (12; 1.0 g, 6.2 mmol) and aniline (13, R═H, 0.57 mL, 6.2 mmol, 1.0 eq) were heated at 160° C. (oil bath) for 12 hours. The reaction was cooled to room temperature and the resulting solid was recrystallized from EtOH to yield 485 mg (31%) of 14 as a yellow-orange crystalline solid: 1H NMR (CDCl3): 8.28 (d, 1H), 7.80-7.67 (m, 2H), 7.60-7.44 (m, 4H), 7.29-7.28 (m, 2H), 2.25 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. customthe resulting solid was recrystallized from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-a3a8e457946541b0b88a48a278e66d0c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09101635B2

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