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

HRID 422038

Reaktionsgleichung

Reaktionsgleichung von HRID 422038
[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]([CH2:24][C:25]#[N:26])[CH:20]=[CH:21][C:22]=1[Cl:23].N>O1CCOCC1.Cl>[Cl:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:24][C:25]1[NH:26][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 3

HCID 222AmmoniaHCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 79336Dimethyl aminoterephthalate

Produkt 1

HCID 136330126Methyl 2-(3,4-dichlorobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 204431481,4-Dioxane hydrochlorideLösungsmittel

Versuchsvorschrift

420 Milligrams of dimethyl aminoterephthalate and 446 mg of 3,4-dichlorophenylacetonitrile were added to 10 mL of 4N hydrogen chloride dioxane solution and stirred for about 2 days. Pouring the reaction mixture into ice, its pH was adjusted to 8-9 with 25% aqueous ammonia. The precipitated crystals were recovered by filtration and washed with water. The crude crystals were dissolved in chloroform-ethyl acetate (1:1) mixed solvent, and after removing the insoluble matter by filtration, the remaining solution was concentrated. The residue was purified on silica gel column chromatography (hexane:ethyl acetate=4:1) to provide 253 mg of the title compound.

Aufarbeitung

  1. additionPouring the reaction mixture into ice, its pH
  2. filtrationThe precipitated crystals were recovered by filtration
  3. washwashed with water
  4. dissolutionThe crude crystals were dissolved in chloroform-ethyl acetate (1:1)
  5. additionmixed solvent
  6. customafter removing the insoluble matter
  7. filtrationby filtration
  8. concentrationthe remaining solution was concentrated
  9. customThe residue was purified on silica gel column chromatography (hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-5444c3375e774297a36f0e4c0ad68e6b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101624B2

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