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CAS No. : | 49584-26-1 | MDL No. : | MFCD00052337 |
Formula : | C7H4ClNO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DBMFYTQPPBBKHI-UHFFFAOYSA-N |
M.W : | 201.63 | Pubchem ID : | 39497 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3261 |
Hazard Statements: | H314-H317 | Packing Group: | Ⅲ |
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 |
---|---|---|
Example 24 4-Cyano-N-(5-chloroquinolin-2-yl)-benzenesulfonamide The title compound was obtained from 3-amino-8-bromoquinoline (Preparation Example 2) and 4-cyanobenzenesulfonyl chloride by the procedure of Example 1. 1H-NMR (CDCl3) delta (ppm): 6.96 (1H, d, J=9.5 Hz), 7.35 (1H, d, J=8.7 Hz), 7.45 (1H, d, J=8.7 Hz), 7.57 (1H, t, J=8.7 Hz), 7.78 (2H, d, J=8.9 Hz), 8.10 (2H, d, J=8.9 Hz), 8.33 (1H, d, J=9.5 Hz). | ||
Synthetic Example 24b 4-Cyano-N-(5-chloroquinoline-2-yl)-benzenesulfonamide The title compound was obtained from 3-amino-8-bromoquinoline (Production Example 2b) and 4-cyanobenzenesulfonyl chloride in the same manner as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 6.96(1H, d, J=9.5Hz), 7.35(1H, d,J=8.7Hz), 7.45(1H, d, J=8.7Hz), 7.57(1H, t J=8.7Hz), 7.78(2H, d, J=8.9Hz), 8.10(2H, d, J=8.9Hz), 8.33(1H, d, J=9.5Hz). | ||
SYNTHETIC EXAMPLE 24b 4-Cyano-N-(5-chloroquinoline-2-yl) -benzenesulfonamide The title compound was obtained from 3-amino-8-bromoquinoline (Production Example 2b) and 4-cyanobenzenesulfonyl chloride in the same manner as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 6.96(1H, d, J=9.5 Hz), 7.35(1H, d, J=8.7 Hz), 7.45(1H, d, J=8.7 Hz), 7.57(1H, tJ=8.7 Hz), 7.78(2H, d, J=8.9 Hz), 8.10(2H, d, J=8.9 Hz), 8.33(1H, d, J=9.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Reference Example 243 4-[2-(2-Fluorophenyl)-4-formyl-1H-pyrrol-1-yl]sulfonyl}benzonitrile To a solution (28 mL) of <strong>[881674-56-2]5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde</strong> (284 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 181 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (992 mg) was added dropwise and the mixture was stirred for 30 min, (4-cyanobenzene)sulfonyl chloride (606 mg) was added, and the mixture was further stirred for 1 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1?2:3) to give the title compound as colorless crystals (yield 420 mg, 79%). 1H-NMR (CDCl3)delta: 6.69 (1H, d, J=1.8 Hz), 6.98-7.04 (1H, m), 7.16-7.18 (2H, m), 7.42-7.49 (1H, m), 7.51-7.54 (2H, m), 7.67-7.71 (2H, m), 8.12 (1H, d, J=1.8 Hz), 9.90 (1H, s). | |
In tetrahydrofuran; | Reference Example 243 4-[2-(2-Fluorophenyl)-4-formyl-1H-pyrrol-1-yl]sulfonyl}benzonitrile To a solution (28 mL) of <strong>[881674-56-2]5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde</strong> (284 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 181 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (992 mg) was added dropwise and the mixture was stirred for 30 min, (4-cyanobenzene)sulfonyl chloride (606 mg) was added, and the mixture was further stirred for 1 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1?2:3) to give the title compound as colorless crystals (yield 420 mg, 79%). 1H-NMR (CDCl3)delta: 6.69 (1H, d, J=1.8 Hz), 6.98-7.04 (1H, m), 7.16-7.18 (2H, m), 7.42-7.49 (1H, m), 7.51-7.54 (2H, m), 7.67-7.71 (2H, m), 8.12 (1H, d, J=1.8 Hz), 9.90 (1H, s). |
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