2-Chloroaniline → 3-(2-Chlorophenyl)-2-(2-ethylcarbamoylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic Acid Ethyl Ester

HRID 1039366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039366
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:32])=[C:8]2[C:13](=[CH:14][C:15]=1[CH3:16])[N:12]=[C:11]([CH2:17][CH2:18][C:19]([O:21]CC)=O)[N:10]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])[C:9]2=[O:31])=[O:5])[CH3:2].C(OC(=O)C1C(C)=C[C:43]([NH:47]C(=O)CCC(OCC)=O)=[C:39](C(O)=O)C=1C)C.ClC1C=CC=CC=1N.P(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:32])=[C:8]2[C:13](=[CH:14][C:15]=1[CH3:16])[N:12]=[C:11]([CH2:17][CH2:18][C:19](=[O:21])[NH:47][CH2:43][CH3:39])[N:10]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])[C:9]2=[O:31])=[O:5])[CH3:2]

Komponenten

7

Edukt 5

HCID 72402-ChloroanilineHCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 671755223-(2-Chlorophenyl)-2-(2-ethoxycarbonylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid ethyl esterHCID 865975834-(3-Ethoxycarbonylpropionylamino)-2,6-dimethylisophthalic acid 1-ethyl ester

Produkt 1

HCID 115906083-(2-Chlorophenyl)-2-(2-ethylcarbamoylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic Acid Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

3-(2-Chlorophenyl)-2-(2-ethoxycarbonylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid ethyl ester: A stirred mixture of 4-(3-ethoxycarbonylpropionylamino)-2,6-dimethylisophthalic acid 1-ethyl ester (0.327 g, 0.89 mmol), 2-chloroaniline (0.28 mL, 2.66 mmol) and phosphorus trichloride (0.74 g, 5.4 mmol) in toluene (6 mL) is heated at 130° C. for 3 h. Upon cooling to room temperature, the reaction mixture is poured onto saturated sodium hydrogen carbonate solution and extracted with chloroform. The chloroform extracts are combined, washed with brine and dried over anhydrous MgSO4. The solvent is removed under reduced pressure and the residue is purified by flash chromatography over silica gel (initial eluent: 19:1 cyclohexane:ethyl acetate; final eluent: 7:3 cyclohexane:ethyl acetate) to afford the title compound.

Aufarbeitung

  1. temperatureUpon cooling to room temperature
  2. extractionextracted with chloroform
  3. washwashed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by flash chromatography over silica gel (initial eluent: 19:1 cyclohexane:ethyl acetate; final eluent: 7:3 cyclohexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-00f1168618d54f7ea38050658f656957
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552015B2

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