Benzylamine → N-Benzyl-(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetamide

HRID 280374

Reaktionsgleichung

[O:1]=[C:2]1[N:14]2[C:5](=[N:6][C:7]3[C:12]([CH2:13]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:4][C:3]1=[CH:15][C:16]([OH:18])=O.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(P(C#N)(CC)=O)C.C(N(CC)CC)C>CN(C)C=O.C1C=CC=CC=1.C(OCC)(=O)C>[CH2:19]([NH:26][C:16](=[O:18])[CH:15]=[C:3]1[S:4][C:5]2=[N:6][C:7]3[C:12]([CH2:13][N:14]2[C:2]1=[O:1])=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a stirred mixture of (3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetic acid (10.5 g, 1.9 mmols) and benzylamine (0.23 g, 2.1 mmols) in 25 ml dimethylformamide at 0° C., was added diethylphosphoryl cyanide (0.28 g, 2.1 mmols) (in dimethylformamide solution), followed by triethylamine (0.41 g, 4.0 mmols). The reaction mixture was stirred for 4 hours at 0° C. and then, at room temperature overnight. The reaction mixture was diluted with benzene-ethyl acetate and washed sequentially with 5% hydrochloric acid, water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The organic solution was dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure to give N-Benzyl-(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetamide which was recrystallized from ethyl acetate. Yield--0.09 g. Mp 258°-259° C.

Aufarbeitung

customat room temperature
customovernight
washwashed sequentially with 5% hydrochloric acid, water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
dry with materialThe organic solution was dried over anhydrous magnesium sulfate
customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-cf5698ff7a884e97b278358b34d4f565
Quelldatensatz: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04588812

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