p-Toluenesulfonic acid → 5,7-dimethoxy-2-(4-morpholinophenyl)quinazolin-4(3H)-one

HRID 336700

Reaktionsgleichung

Reaktionsgleichung von HRID 336700
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[N:15]1([C:21]2[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.S([O-])(O)=O.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C.O>[CH3:14][O:13][C:7]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:6][C:25]([C:24]1[CH:23]=[CH:22][C:21]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:28][CH:27]=1)=[N:1]2

Komponenten

7

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 2913494-MorpholinobenzaldehydeHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium Bisulfite

Produkt 1

HCID 1360380255,7-dimethoxy-2-(4-morpholinophenyl)quinazolin-4(3H)-oneAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
155 °C

Versuchsvorschrift

A mixture of 2-amino-4,6-dimethoxybenzamide (0.15 g, 0.765 mmol), 4-morpholin-4-yl-benzaldehyde (0.15 g, 0.765 mmol), sodium hydrogensulfite (0.136 g, 0.765 mmol) and p-toluenesulfonic acid (10 mg) in N,N-dimethyl acetamide (10 mL) was stirred at 155° C. for 14 h. The reaction mixture was cooled to room temperature and diluted with water (50 mL). The solid was collected by filtration, washed with water and MeOH to yield 5,7-dimethoxy-2-(4-morpholinophenyl)quinazolin-4(3H)-one (0.109 g, 39%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solid was collected by filtration
  3. washwashed with water and MeOH

Quellen und Nachweise

ORD-Eintrag
ord-4494ed692c544569881c4e724697ef88
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889698B2

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