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CAS No. : | 20028-68-6 | MDL No. : | MFCD08445622 |
Formula : | C8H3Cl3N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VUPOGEZMJNDSHI-UHFFFAOYSA-N |
M.W : | 233.48 | Pubchem ID : | 10421510 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 2,3-Dimethylaniline In diethyl ether; water; trichlorophosphate | Part C: The preparation of 2,4,6-trichloroquinazoline. A mixture of 6-chloro-2,4-quinazolinedione (3.27 g) in 30 mL of phosphorous oxychloride and 1.5 mL of dimethylaniline was refluxed for 41/2 hours. The reaction was cooled to room temperature and was poured into a 0° C. mixture of 300 mL of diethyl ether and 300 mL of water. The ether layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to yield 3.54 g of a brown/yellow solid (91percent): 1 H NMR (DMSO-d6, 300 MHz) δ8.325 (m, 1H), 8.20 (m, 1H), 8.085 (m, 1H). |
73% | Stage #1: at 20℃; for 0.5 h; Stage #2: for 14 h; Reflux |
General procedure: A mixture of quinazoline-2,4(1H,3H)-dione 4a (0.48 g, 2.96 mmol) in POCl3 (3.31 mL,35.52 mmol) was stirred at room temperature for 30 min. AfterN,N-diethylaniline (0.167 mL, 0.86 mmol) was added drop-wise,the reaction mixture was heated to reflux for 14 h. After cooling to rt, remained POCl3 was removed under reduced pressure. Thereaction residue was extracted three times with CH2Cl2 (30 mL),dried over MgSO4, concentrated under reduced pressure, and purifiedby column chromatography (EtOAc/n-Hex = 1:9) on silica gelto get the title product 5a in 87percent yield (513 mg). |
69% | With trichlorophosphate In 1,4-dioxane at 120℃; | Into a 50-mL round-bottom flask, was placed a solution of 6-chloroquinazohne-2,4(lH,3H)-dione (2 2 g, 11 22 mmol, 1 00 equiv) ui 1,4-dioxane (20 mL), phosphoryl tπchlonde (17 g, 111 84 mmol, 1000 equiv) The resulting solution was stirred overnight at 120°C m an oil bath The resulting mixture was concentrated under vacuum The reaction was then quenched by the addition of 200 mL of water The resulting solution was extracted with 3x200 mL of ethyl acetate and the organic layers combined The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 50) This resulted in 1 8 g (69percent) of 2,4,6- tπchloroqumazohne as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.2% | With trichlorophosphate In <i>N</i>,<i>N</i>-dimethyl-aniline for 3 h; Reflux | 2,4-Dihydroxy-6-chloroquinazoline (M1) (16.0 g, 0.081 mol) was added to the reaction flask.Add phosphorus oxychloride (47 ml, 0.515 mol),N,N-dimethylaniline (31 ml, 0.243 mol) was added dropwise with stirring at room temperature for 3 hours under reflux.Stop heating,Pour into 500ml of ice water.Precipitating a brownish black solid,Filtering,dry,Column chromatography (petroleum ether - ethyl acetate) to give a pale yellow solid 8.74g, yield 46.2percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49.5% | for 1 h; Reflux | 5-Chloro-2-aminobenzoic acid (0.429 g, 2.5 mmol), urea (0.33 g, 5.5 mmol), phosphorus pentachloride (3.124 g, 15 mmol) and phosphorus oxychloride (10 mL) were added and the reaction was stopped by heating to reflux for 1 h. Decompression to steam Excess phosphorus oxychloride, the residue was dissolved in methylene chloride, ice water was washed with phosphorus oxychloride and phosphorus pentachloride, the separation of water The organic phase was adjusted to pH 6-7 with saturated sodium bicarbonate and extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate. Concentration column chromatography gave 0.289 g of a light yellow solid, yield: 49.5percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | for 16 h; Reflux | A mixture of POCl3 (10 mL) and DMF (4 drops) was stirred at ambient temperature for 30 min, prior to its addition to a flask containing 5-chloroquinazoline-2,4(1H,3H)-dione monopotassium salt (594 mg, 2.53 mmol). The mixture was heated to gentle reflux for 16 h. The resulting dark orange solution was cooled to ambient temperature and poured into ice water. A dark brown oil formed that on stirring formed a brown precipitate. The suspension was filtered and washed with copious water. Most of the precipitate was transferred to a round-bottomed flask, and the remainder washed off the sinter with THF (80 mL). The THF washings were added to the flask and concentrated. The residual solid was then dissolved in boiling IMS, filtered and the filtrate concentrated to afford the title compound as a light brown solid (132 mg, 22percent).1H NMR (DMSO): 8.56 (1H, dd, J 2.4 and 0.5), 8.41 (1H, dd, J 9.0 and 2.3) and 8.30 (1H, dd, J 9.1 and 0.5). |
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