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

HRID 422037

Reaktionsgleichung

Reaktionsgleichung von HRID 422037
[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

5

Edukt 4

HCID 222AmmoniaHCID 73722m-ChlorophenylacetonitrileHCID 79336Dimethyl aminoterephthalateHCID 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.

Aufarbeitung

  1. customstirring at 30° C.
  2. customfor 63 hours
  3. waitat 70° C. for 25 hours
  4. additionice was added to the reaction mixture
  5. customWhereupon precipitated crystals
  6. filtrationwere recovered by filtration
  7. washwashed with water, ether and chloroform by the order
  8. customto through-flow drying
  9. temperatureunder heating

Quellen und Nachweise

ORD-Eintrag
ord-d0a4eba0fc884d528c766ca2cd67e528
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101624B2

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