Identification | Back Directory | [Name]
2,4-Dichloro-6-methoxyquinazoline | [CAS]
105763-77-7 | [Synonyms]
2,4-Dichloro-6-methoxyqui... 2,4-Dichloro-6-methoxyquinazoline 6-Methoxy-2,4-dichloroquinazoline Quinazoline,2,4-dichloro-6-methoxy- | [Molecular Formula]
C9H6Cl2N2O | [MDL Number]
MFCD09954880 | [MOL File]
105763-77-7.mol | [Molecular Weight]
229.06 |
Chemical Properties | Back Directory | [Melting point ]
171 °C | [Boiling point ]
315.9±24.0 °C(Predicted) | [density ]
1.450 | [storage temp. ]
Inert atmosphere,2-8°C | [pka]
-0.67±0.30(Predicted) | [Appearance]
Off-white to light yellow Solid | [InChI]
InChI=1S/C9H6Cl2N2O/c1-14-5-2-3-7-6(4-5)8(10)13-9(11)12-7/h2-4H,1H3 | [InChIKey]
WEAMQTSRMCCGSJ-UHFFFAOYSA-N | [SMILES]
N1=C2C(C=C(OC)C=C2)=C(Cl)N=C1Cl |
Hazard Information | Back Directory | [Synthesis]
Method F1: Synthesis of 2,4-dichloro-6-methoxyquinazoline (xa)
To a mixture of 6-methoxyquinazoline-2,4(1H,3H)-dione (9.63 g, 50.2 mmol) and phosphorus trichloride (POCl3, 150 mL) was added N,N-dimethylaniline (0.5 mL). The reaction mixture was stirred at 120 °C for 2 hours. Upon completion of the reaction, the excess POCl3 was removed by distillation under reduced pressure. the residue was slowly poured into ice water and the pH was adjusted to about 7 by slowly adding saturated sodium bicarbonate (NaHCO3) solution at 0 °C, where a precipitate was formed. The precipitate was collected and dried under vacuum to give 2,4-dichloro-6-methoxyquinazoline (11.2 g, 98% yield) as a brown solid.
LCMS m/z = 229.1, 231.0 [M + 1] (Method B) (retention time = 1.87 min).
1H-NMR (400 MHz, DMSO-d6): δ 7.89 (d, J = 9.2 Hz, 1H), 7.71 (dd, J = 8.8, 2.4 Hz, 1H), 7.38 (d, J = 1.6 Hz, 1H), 3.91 (s, 3H). | [References]
[1] Patent: US2015/307477, 2015, A1. Location in patent: Paragraph 1497 [2] Patent: JP6121658, 2017, B2. Location in patent: Paragraph 1096; 1099 [3] Patent: US2010/68197, 2010, A1. Location in patent: Page/Page column 17 [4] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 11, p. 2439 - 2444 [5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7717 - 7727 |
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