Water → 4-Chloro-7-methylquinazoline

HRID 1432844

Reaktionsgleichung

Reaktionsgleichung von HRID 1432844
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.P(Cl)(Cl)([Cl:22])=O.O>C1(C)C=CC=CC=1>[Cl:22][C:6]1[C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][N:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1354525337-Methyl-4(3H)-quinazolinone

Produkt 1

HCID 219420144-Chloro-7-methylquinazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 7-methyl-3H-quinazolin-4-one (10.6 g, 69 mmol) in toluene (350 mL) is added triethylamine (17.5 g, 173 mmol) followed by phosphorous oxychloride (12.3 g, 80 mmol). The resulting solution is heated to 80° C. After 4 hours, the solution is cooled to ambient temperature. The reaction mixture is poured into 500 mL of water. The layers are separated and the organic layer is washed with H2O, saturated NaHCO3, and saturated NaCl, dried over MgSO4, filtered and concentrated. The resulting crude product is purified by recrystallization from EtOAc. The title compound is obtained as a white solid (10 g, 56 mmol). 1H NMR (CDCl3, 300 MHz) δ9.02 (s, 1H), 8.16 (d, 1H), 7.87 (s, 1H), 7.55 (d, 1H), 2.62 (s, 3H).

Aufarbeitung

  1. temperaturethe solution is cooled to ambient temperature
  2. customThe layers are separated
  3. washthe organic layer is washed with H2O, saturated NaHCO3, and saturated NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude product is purified by recrystallization from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-c99e29bc5508448993712c48483b72e9
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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