Thionyl Chloride → 2-(3-Dimethylamino-butyl)-1-phenyl-1H-quinazolin-4-one

HRID 557123

Reaktionsgleichung

[CH3:1][N:2]([CH:4]([CH2:8][CH2:9][CH3:10])[C:5](O)=O)[CH3:3].S(Cl)(Cl)=O.[C:15]1([NH:21][C:22]2[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=2[C:24]([NH2:26])=[O:25])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClC(Cl)Cl>[CH3:1][N:2]([CH3:3])[CH:4]([CH3:5])[CH2:8][CH2:9][C:10]1[N:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:22]2[C:23]([C:24](=[O:25])[N:26]=1)=[CH:27][CH:28]=[CH:29][CH:30]=2

Komponenten

Reaktionsbedingungen

Temperatur: 57.5 °C

Versuchsvorschrift

3.80 g (20.9 mmol) dimethylamino-pentanoic acid were added to 25 ml thionyl chloride and stirred for 90 min. at 55-60° C. The remaining thionyl chloride was distilled in vacuum and the residue was added to a solution of 2.00 g (9.42 mmol) 2-phenylamino-benzamide (see above) in 30 ml trichloromethane at 0° C. The reaction mixture was boiled for 4 h and stirred overnight at room temperature. The residue was filtrated and dissolved in dichloromethane and saturated sodium bicarbonate solution. The organic solvent was dried over magnesium sulfate and evaporated. The yellow oil slowly crystallized.

Aufarbeitung

distillationThe remaining thionyl chloride was distilled in vacuum
waitThe reaction mixture was boiled for 4 h
stirringstirred overnight at room temperature
filtrationThe residue was filtrated
dissolutiondissolved in dichloromethane
dry with materialThe organic solvent was dried over magnesium sulfate
customevaporated
customThe yellow oil slowly crystallized

Quellen und Nachweise

ORD-Eintrag: ord-2c9c8312544845c88e1ce53cde67ccbd
Quelldatensatz: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08058431B2

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