p-Toluenesulfonic acid → 2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-5-methoxy-3H-quinazolin-4-one

HRID 591714Notizen

Reaktionsgleichung

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([NH2:6])=[O:5].[OH:13][CH2:14][CH2:15][O:16][C:17]1[C:24]([CH3:25])=[CH:23][C:20]([CH:21]=O)=[CH:19][C:18]=1[CH3:26].OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[OH:13][CH2:14][CH2:15][O:16][C:17]1[C:24]([CH3:25])=[CH:23][C:20]([C:21]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][CH:9]=[CH:8][C:7]=3[O:11][CH3:12])[N:1]=2)=[CH:19][C:18]=1[CH3:26]

Komponenten

Reaktionsbedingungen

Temperatur: 115 °C

Versuchsvorschrift

To a solution of 2-amino-6-methoxy-benzamide (1.00 g, 6.01 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (1.28 g, 6.59 mmol) in N,N-dimethylacetamide (15 mL) were added NaHSO3 (58.5 wt %, 0.68 g, 6.50 mmol) and p-TSA (0.23 g, 1.20 mmol) and the reaction mixture was heated at 115° C. for 20 hours, and cooled to room temperature. N,N-dimethylacetamide was removed under reduced pressure. The residue was diluted with water (50 mL), stirred for 30 minutes, and then filtered. The solid was suspended in dichloromethane (30 mL), stirred for 1 h, filtered, and dried under vacuum to give 2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-5-methoxy-3H-quinazolin-4-one as an off-white solid. Yield: 1.1 g (55%).

Aufarbeitung

temperaturecooled to room temperature
customN,N-dimethylacetamide was removed under reduced pressure
additionThe residue was diluted with water (50 mL)
filtrationfiltered
stirringstirred for 1 h
filtrationfiltered
customdried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-307d8d6ba4044e98a6195850d6139bf0
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09238640B2

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