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CAS No. : | 98-60-2 | MDL No. : | MFCD00007439 |
Formula : | C6H4Cl2O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZLYBFBAHAQEEQQ-UHFFFAOYSA-N |
M.W : | 211.07 | Pubchem ID : | 7398 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 | UN#: | 3261 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
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 |
---|---|---|
With triethylamine; In acetonitrile; at 40℃; for 8 - 12h; | To a solution of (S) -isoleucinol (17.6 mg, 0.15 mmol) in CH3CN (600 muL) was added Et3N (300 I1L, 1M in CH3CN) and 4-CHLOROBENZENESULFONYL chloride (21.07 mg, 0.1 mmol) as a solution in CH3CN (400 1L). The vial was capped and shaken for 8 to 12 hours at 40 °C. The solvent was removed, and the oil was dissolved in EtOAc (1 mL). The resulting solution was washed with 1M HC1 (2 x LML). The solvent was removed in vacuo, and the residue dissolved in 1.6 ML DMSO (0.03 M). | |
With triethylamine; In acetonitrile; at 25℃; for 0.5h; | To a solution OF 4-CHLOROBENZENESULFONYL chloride (1.93 g, 9.1 mmol) in CH3CN (25 mL) and (S) -isoleucinol (1.07 g, 9.1 mmol) was added Et3N (1.91 mL, 13.7 mmol). The reaction mixture was stirred at 25 °C for 30 minutes. The solvent was removed and the oil was dissolved in CH2C12 (20 mL). The solution was washed with water (2 x 20 mL) and dried over NA2S04. The solvent was removed to give N-4- chloro benzenesulfonyl isoleucinol, which was carried on without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; | Synthetic Example 84b 6-(4-Chlorobenzenesulfonylamino)-1-cyanoisoquinoline The compound obtained using <strong>[23687-26-5]6-aminoisoquinoline</strong> (0.5 g, Synthesis, 733 (1975)) and 4-chlorobenzenesulfonyl chloride (0.88 g) in the same method as in Synthetic Example 1b was dissolved in chloroform (150 ml). Under ice-cooling, m-chloroperbenzoicacid (0.9 g) was added theterto, followed by stirring at room temperature overnight. The solvent was evaporated, and the resulting crystals were washed with diethyl ether, collected by filtration and dried, to give 6-(4-chlorobenzenesulfonylamino)isoquinoline-N-oxide (1.072 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.93% | With dmap; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 5℃; for 2h; | Add III-3 (1.00g, 6.29mmol), DMAP (154mg, 1.26mmol), DIEA (3.12mL, 18.87mmol) to 100mL three-necked flask, stir and dissolve with 10mL acetonitrile, slowly add at 05C 4-chlorophenylsulfonyl chloride (IV-5, 1.60g, 7.55mmol) in 10mL acetonitrile solution, after the addition was completed, stirring was continued for 2 hours under low temperature conditions.TLC monitoring of raw material reactionsCompletely, concentrate the reaction solution, dissolve with 30 mL of ethyl acetate, wash with 40 mL of water, and then extract twice with ethyl acetate (20 mL×2). The organic phase is combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate The filtrate is spin-dried and subjected to column chromatography (petroleum ether:Ethyl acetate = 10:1 rinse),After drying, 1.71 g of a brownish yellow solid V-11 was obtained.The yield was 91.93%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; at 20.0℃; for 16.0h; | 3-(Pyridin-2-yl)- 1 ,2,4-thiadiazol-5-amine (50 rag, 0.28 mmoi) was dissolved in 1.5 ml, pyridine. 4-Chlorobenzenesulfonyl chloride (65 mg, 0.31 mmol) was then added. The mixture was stirred for 16 hours at room temperature. The reaction was partitioned between dichloroniethane and water. The aqueous layer was extracted with dichloromethane. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to obtain Compound 14 as a tan solid. LCMS (M/Z): 352 (M + H). NMR (400 MHz, acetone) delta ppm 7.53 - 7.63 (m, 3 H) 7.91 (d, J 8.64 Hz, 2 H) 8.03 (td, J=7.75, 1.54 Hz, 1 H) 8.24 (d, J 8.00 Hz, 1 IT) 8.66 (d, J 4.49 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With pyridine; In dichloromethane; at 0 - 20℃; for 16h; | To a solution of intermediate 99-i in DCM (0.5 M) at 0°C was addedchlorobenzenesulfonylchloride (1.2 eq) and pyridine (2.0 eq). The reaction was allowed to warm to rt and stirred for 16 h. The solution was concentrated under reduced pressure and the residue was taken up in saturated NaHCC>3. The resulting mixture was extracted with 2x 10 mL EtOAc and the combined organics were washed with saturated NaHCC>3, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The1 crude material could be purified by recrystallization from DCM (35 mg, 36percent). H NMR(400 MHz, DMSO-de) delta 11.06 (s, 1H), 7.83 (d, J = 8.6 Hz, 2H), 7.78 - 7.61 (m, 3H), 7.47 (d, J = 2.4 Hz, 1 H), 7.28 (dd, J = 8.8, 2.4 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium carbonate; In dichloromethane; at 0 - 20℃; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in dichloromethane (20 mL), and the substituted benzoylchloride or sulfonyl chloride (2.0 mmol) was added. The reactionmixture was stirred at 0 C for 1e2 h until TLC analysisshowed completion of the reaction. Then the solvent was washedsuccessively with water (20 mL), brine (20 mL). The organic layerwas concentrated and purified by flash column chromatography onsilica gel with CH2Cl2/CH3OH as the eluent to get target compounds3aeb or 4aee. |
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