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CAS No. : | 50377-49-6 | MDL No. : | MFCD11046864 |
Formula : | C11H11ClN2O2 | Boiling Point : | 286.8±40.0°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 238.67 | Pubchem ID : | 10490150 |
Synonyms : |
|
TPSA :Topological Polar Surface Area | 44.2 | H-Bond Acceptor Count : | 4 |
XLogP3 : | 2.8 | H-Bond Donor Count : | 0 |
SP3 : | 0.27 | Rotatable Bond Count : | 2 |
Signal Word: | Warning | Class | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 80℃; for 1.00 h; | 2.50 g (1 1.4 mmol) of 6,7-dimethoxy-2-methylquinazolin-4-ol were suspended in 1 1.00 mL of thionyl chloride, admixed with 10 drops of N,N-dimethylformamide and stirred for 1 h at 80°C. The thionyl chloride was removed in vacuo. The residue was admixed twice with in each case 20 mL of toluene and evaporated to dryness in vacuo. With ice bath cooling, 20 mL of a 5N sodium hydroxide solution were added dropwise to the residue. The suspension was admixed with 20 mL of dichloromethane and vigorously stirred for 10 min. The phases were separated and the aqueous phase was extracted by shaking five times with in each case 20 mL of dichloromethane. The combined organic phases were dried over sodium sulphate, filtered and evaporated to dryness in vacuo. 2.71 g (100percent of theory) of the title compound were isolated as a beige solid. 1H-NMR (400 MHz, CDCI3): δ [ppm] = 2.79 (s, 3H), 4.04 (s, 3H), 4.05 (s, 3H), 7.25 (s, 1H), 7.35 (s, 1H). LC-MS (method 1): Rt = 3.19 min; MS (ESI/APCIpos) m/z = 239.1 [M+H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | for 3.00 h; Reflux | Step b 4-Chloro-6,7-dimethoxy-2-methylquinazoline A mixture of 6,7-dimethoxy-2-methylquinazolin-4(3H)-one (1.0 mg) and phosphorous oxychloride (20 mL) was refluxed for 3 h. The reaction mixture was attained to rt and poured into ice cold water and stirred for 10 min. The solution was extracted with chloroform (3*100 mL) and the combined CHCl3 layer was washed water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent to give the product as a yellow color solid (1.0 g, 92percent), mp 182-184° C. 1H NMR (400 MHz, CDCl3): δ 7.36 (1H, s), 7.30 (1H, s), 4.06 (6H, s), 2.81 (3H, s); LC-MS (positive ion mode): m/z 239, 241 (M+H)+. |
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