Hydrochloric Acid → 2-(pyridin-3-yl)-4-(2-chloro-4-fluorophenyl)-7,7-dimethyl-4,6,7,8-tetrahydroquinazolin-5(1H)-one

HRID 1929537

Reaktionsgleichung

Reaktionsgleichung von HRID 1929537
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([NH2:10])=[NH:9])[CH:3]=1.[Cl:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH:14]=O.[CH3:21][C:22]1([CH3:30])[CH2:27][C:26](=[O:28])[CH2:25][C:24](=O)[CH2:23]1.C([O-])(=O)C.[Na+].Cl>C(O)C.O.C(OCC)(=O)C>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[NH:10][C:24]3[CH2:23][C:22]([CH3:30])([CH3:21])[CH2:27][C:26](=[O:28])[C:25]=3[CH:14]([C:13]3[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:12]=3[Cl:11])[N:9]=2)[CH:3]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 31358DimedoneHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 202042Nicotinamidine hydrochlorideHCID 517045Sodium Acetate

Produkt 1

HCID 250302952-(pyridin-3-yl)-4-(2-chloro-4-fluorophenyl)-7,7-dimethyl-4,6,7,8-tetrahydroquinazolin-5(1H)-oneAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-Pyridinecarboxamidine hydrochloride (Schaefer F. C., Peters G. A., et al. J. Org. Chem.; 1961; 26(2); 412-418.) 2.164 mmol, 2-chloro-4-fluorobenzaldehyde 2.164 mmol, 5,5-dimethyl-1,3-cyclohexanedione 2.164 mmol and sodium acetate 3.2 mmol were reacted in 8 ml of anhydrous ethanol under refluxing for 18 hr, condensed, and ethyl acetate and water and 1N HCl were added to separate the layers. The water layer was adjusted with concentrated NaOH solution until the pH to be basic, then ethyl acetate was added and extracted twice. The organic layers were combined, dried over anhydrous sodium sulfate and separated by column chromatography to obtain a yellow solid of 0.22 g (yield 26%); mp 186-187° C. 1H-NMR (400 MHz, CDCl3) δ 1.15 (3H, s, CH3); 1.16 (3H, s, CH3); 2.31 (2H, s, CH2); 2.53-2.69 (2H, m, CH2); 6.07 (1H, s, CH); 6.94-6.96 (1H, m, ArH); 7.14-7.17 (1H, m, ArH); 7.23-7.26 (1H, m, ArH); 7.34-7.38 (1H, m, ArH) 8.07-8.09 (1H, m, ArH); 8.69-8.71 (1H, m, ArH); 8.89 (1H, m, ArH). MS (EI) 383.1 (M+).

Aufarbeitung

  1. temperatureunder refluxing for 18 hr
  2. additionwere added
  3. customto separate the layers
  4. additionethyl acetate was added
  5. extractionextracted twice
  6. dry with materialdried over anhydrous sodium sulfate
  7. customseparated by column chromatography
  8. customto obtain a yellow solid of 0.22 g (yield 26%)

Quellen und Nachweise

ORD-Eintrag
ord-f0135dcc23d648ad9493a2fc9e0c3f90
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188091B2

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