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CAS No. : | 3739-94-4 | MDL No. : | MFCD00006289 |
Formula : | C7H3Cl2NO2 | Boiling Point : | - |
Linear Structure Formula : | C5H3N(CO)2Cl2 | InChI Key : | GWHOGODUVLQCEB-UHFFFAOYSA-N |
M.W : | 204.01 | Pubchem ID : | 77335 |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3261 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
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* 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 |
---|---|---|
71% | With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;Schlenk technique; Inert atmosphere; | To a solution of <strong>[1709-71-3]3-(acryloyloxy)-2-hydroxypropyl methacrylate</strong> (3g; AHM, 3.94 g, 8.98 mmol) and Et3N (2.6 mL, 1.9 g,18.9 mmol) in anhydrous CH2Cl2 (20 mL) was slowly added a solution of pyridine-2,6-dicarbonyl dichloride (1.83 g, 8.98 mmol) in anhydrous CH2Cl2 (20 mL) at 0 C. The slightly turbid mixture was stirred at r.t. for 16 h, filtered through Celite, and concentrated in vacuo under addition of MEHQ as polymerization inhibitor. The crude product was purified by flash chromatography (hexanes-EtOAc, 3:1 ? 2:1) to yield 8g (3.56 g, 6.36 mmol, 71%) as a clear colorless oil; Rf = 0.21 (hexanes-EtOAc, 2:1). FT-IR (ATR): 2931 (w), 2184 (w), 1962 (w), 1720 (s), 1293 (m),1236 (m), 1162 cm-1 (s). 1H NMR (300 MHz, CDCl3): delta = 1.93 (s, 6 H, CH3), 4.41-4.69 (m,8 H, OCH2), 5.59-5.62 (m, 2 H, cis-3?-H), 5.65-5.73 (m, 2 H,OCH), 5.85-5.91 (m, 2 H, cis-3??-H), 6.08-6.21 (m, 4 H, trans-3?-H,2??-H), 6.40-6.49 (m, 2 H, trans-3??-H), 7.99-8.04 (m, 1 H, 4-H),8.23-8.26 (m, 2 H, 3-H, 5-H). 13C NMR (75 MHz, CDCl3): delta = 18.2 (CH3), 62.4 (OCH2), 71.0(OCH), 126.6 (C-3?), 127.6 (C-2??), 128.2 (C-3, C-5), 131.9 (C-3??),135.6 (C-2?), 138.3 (C-4), 148.1 (C-2, C-6), 163.3 (Ar-C=O), 165.6(C-1??), 166.7 (C-1?). MS (ESI): m/z = 582.2 [M + Na]+, 560.2 [M + H]+, 197.1 [C10H13O4(AHM - OH)]+.HRMS (ESI): m/z calcd for C27H29NO12: 582.1582; found: 582.1586 [M + Na]+. |