Ammonia → Methyl 2-(3-chlorobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate

Reaktionsgleichung

[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[Cl:16][C:17]1[CH:18]=[C:19]([CH2:23][C:24]#[N:25])[CH:20]=[CH:21][CH:22]=1.O1CCOCC1.Cl.N>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=1)[CH2:23][C:24]1[NH:25][C:4](=[O:6])[C:3]2[C:2](=[CH:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=2)[N:1]=1

Komponenten

Edukt 4

HCID 222Ammonia

HCID 73722m-Chlorophenylacetonitrile

HCID 79336Dimethyl aminoterephthalate

HCID 204431481,4-Dioxane hydrochloride

Produkt 1

HCID 136330125Methyl 2-(3-chlorobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylateAusbeute 67,9 %

Versuchsvorschrift

A mixture of 628 mg of dimethyl aminoterephthalate, 546 mg of 3-chlorophenylacetonitrile and 15 mL of 4N hydrogen chloride dioxane solution was stirred at room temperature for 7 hours. Further continuing the stirring at 30° C. for 63 hours and at 70° C. for 25 hours, ice was added to the reaction mixture, followed by addition of 7 mL of 25% aqueous ammonia. Whereupon precipitated crystals were recovered by filtration, and washed with water, ether and chloroform by the order stated. Subjecting the crystals to through-flow drying under heating, 670 mg of the title compound was obtained.