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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 : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.54 |
TPSA : | 42.52 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.28 cm/s |
Log Po/w (iLOGP) : | 1.81 |
Log Po/w (XLOGP3) : | 1.84 |
Log Po/w (WLOGP) : | 3.35 |
Log Po/w (MLOGP) : | 2.11 |
Log Po/w (SILICOS-IT) : | 1.99 |
Consensus Log Po/w : | 2.22 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.65 |
Solubility : | 0.478 mg/ml ; 0.00226 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.35 |
Solubility : | 0.935 mg/ml ; 0.00443 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.56 |
Solubility : | 0.058 mg/ml ; 0.000275 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.76 |
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 |
---|---|---|
71% | at 30 - 60℃; | 1L three bottles were added 500mL concentrated H2SO4, p-chlorobenzenesulfonyl chloride 190g (0.9mol, 1eq) and heated to 30 ° C, dropping fuming nitric acid 56. 7g (0. 9mo 1,1 eq) to keep the temperature below 60 ° C, After the addition the internal temperature was stirred overnight at 55 ° C, TLC (PE / EA = 10/1). The reaction was cooled, poured into ice water, extracted with DCM, dried, filtered and concentrated to give 3-nitro-4-chlorobenzenesulfonyl chloride, white crystals 163g, yield 71percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium carbonate; sodium sulfite In water at 50℃; for 2 h; | General procedure: A solution of sodium sulfite (17.93g, 142.26 mmol) in H2O (100 ml) was stirred at room temperature for10 min. Sodium carbonate (23.90 g, 284.52 mmol)was added to the stirred solution.The resulting solution was stirred at 50 °C for 10 minutes.cyclopropanesulfonyl chloride (20 g, 142.26 mmol) was added dropwise to thesolution and was stirred at 50 °C for 2 hours. Thereaction mixture was evaporated to dryness and redissolved in EtOH (200 ml). The suspension was allowed to stir at roomtemperature for 20 min. The suspension was filtered and the filtrate evaporatedto afford a white solid, this was stirred with MeCN (50 ml) and thenfiltered to afford sodium cyclopropanesulfinicacid (13.70 g, 75 percent) as a white solid. 1H NMR (400.132 MHz, DMSO d6)δ 1.38-1.31 (m, 1H), 0.27-0.24 (m,2H) and 0.08-0.03 (m, 2H). |
4.3 g | With sodium sulfite In water at 80 - 90℃; for 1 h; | To chlorosulfonic acid (10 g, 86 mmol), chlorobenzene(3.23 g,28 mmol) was added dropwise, not to increase temperature over 20°C. The solution was stirredat room temperature by 1 hour and it was slowly poured onto ice (50 g). The precipitate wasfiltered off, washed with water and added portionwise to the solution ofnatrium sulfite (7.5 g,60 mmol) in water (28 mL) at temp. 80°C.The mixture was stirred at 90°Cby 1 hour and 50percent natrium hydroxide was slowly dropped to maintain pH= 8-9. Thehot mixture was filtered off and the filtrate was keep at room temperature for10 hours. The white crystals of product 4-chlorobenzenesulfinate natrium saltwas filtered off, washed by cold water and dried at room temperature. Product 3was obtained in 75percent yield (4.3 g). IR (cm–1): 1575 (CHar); 1340,1130 (SO2); 1004, 981 (CH); 832, 740 (CCl). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.3% | With triethylamine In dichloromethane at 0 - 20℃; | General procedure: To a stirred solution of 7-chloro-4-piperazin-1-yl-quinoline (2) (0.25 g, 1 mmol) in 8–10 mL of DCM at 0 °C was added triethylamine (0.12 mL, 1.26 mmol). Different aryl sulfonyl chlorides (1 mmol) were added dropwise/portion wise and the resulting solution was stirred further for 15 min at 0 °C and then stirred at room temperature for different time intervals. On reaction completion (TLC), the reaction mix was diluted with 20 mL water and 20 mL DCM and partitioned in separating funnel, where the organic layer was washed with water (3 × 20 mL) before being separated and dried over sodium sulfate to yield compound 3 in which was recrystallized in DCM:Hexane to yield pure products in 85–95percent yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With sulfuric acid; nitric acid; at 30 - 60℃; | 1L three bottles were added 500mL concentrated H2SO4, p-chlorobenzenesulfonyl chloride 190g (0.9mol, 1eq) and heated to 30 C, dropping fuming nitric acid 56. 7g (0. 9mo 1,1 eq) to keep the temperature below 60 C, After the addition the internal temperature was stirred overnight at 55 C, TLC (PE / EA = 10/1). The reaction was cooled, poured into ice water, extracted with DCM, dried, filtered and concentrated to give 3-nitro-4-chlorobenzenesulfonyl chloride, white crystals 163g, yield 71% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | To a solution of S-cyclohexylglycine (1.00 g, 5.16 mmol) in H2O (10 mL) and THF (11 mL) was added 4-CHLOROBENZENESULFONYL chloride (1.53 g, 7.23 mmol) followed by 2. 5N NAOH (8.26 mL) at 25C with stirring. After 24 hours, the reaction was quenched by addition of 6 N HC1 until pH=2. The reaction mixture was then extracted with EtOAc (2x50 mL). The combined organic extracts were washed with saturated brine (2X50 mL), dried over MGS04, and evaporated to afford a white solid. This white solid was taken up in ET20, filtered and evaporated to afford an amorphous white solid which after washing with hexane afforded 0.90 g (52%) of product, mp 120-128C. Mass Spectrum (+ESI): 354 ([M+Na]+). Anal: Calc'd for CI4HL8CLN04S : C, 50.68 ; H, 5.47 ; N, 4.22. Found: C, 50.59 ; H, 5.46 ; N, 4.19. |
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 |
---|---|---|
With triethylamine; In dichloromethane; at 0 - 20℃; | To a solution of D-(-)-2-Amino-2-phenyl-acetamide (6.0 g, 40 mmol) in 150 mL of methylene chloride is added triethylamine (6.9 mL, 50 mmol) and 4-chlorobenzensulfonylchloride (8.43 g, 40 mmol) at 0° C. The reaction is warmed to room temperature and stirred overnight. The reaction is quenched with sodium bicarbonate and methylene chloride is added. The solid is filtered, washed with water and ether and dried in vacuo to provide 12.3 g of the title compound. C13 NMR (100 MHz, CD3OD) 60.3, 127.3, 128.1, 128.4, 128.7, 128.9, 137.1, 138.5, 139.7, 172.9. MS 325.1 m/z (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 69 1-Chloro-6-(4-chlorobenzenesulfonylamino)isoquinoline The title compound was obtained by the procedure of Example 1, except using <strong>[347146-33-2]6-amino-1-chloroisoquinoline</strong> (Preparation Example 23) and 4-chlorobenzenesulfonyl chloride. 1H-NMR (CDCl3) delta (ppm): 7.33 (1H, brs), 7.39 (1H, dd, J=2.0, 8.8 Hz), 7.44 (2H, d, J=8.8 Hz), 7.50 (1H, d, J=5.6 Hz), 7.58 (1H, d, J=2.0 Hz), 7.81 (2H, d, J=8.8 Hz), 8.24 (1H, d, J=5.6 Hz), 8.25 (1H, d, J=8.8 Hz). FAB-MS: 353. | ||
Synthetic Example 62b 1-Chloro-6-(4-chlorobenzenesulfonylamino)isoquinoline The title compound was obtained using 6-amino-1-chloro-isoquinoline (Production Example 23b) and 4-chlorobenzenesulfonyl chloride in the same method as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm):7.33(1H, brs), 7.39(1H, dd, J=2.0, 8.8Hz), 7.44(2H, d, J=8.8Hz), 7.50(1H, d, J=5.6Hz), 7.58(1H, d, J=2.0Hz), 7.81(2H, d, J=8.8Hz), 8.24(1H, d, J=5.6Hz), 8.25(1H, d, J=8.8Hz). FAB-MS: 353. | ||
SYNTHETIC EXAMPLE 62b 1-Chloro-6-(4-chlorobenzenesulfonylamino)isoquinoline The title compound was obtained using 6-amino-1-chloro-isoquinoline (Production Example 23b) and 4-chlorobenzenesulfonyl chloride in the same method as in Synthetic Example 1b. 1H-NMR(CDCl3) delta (ppm): 7.33(1H, brs), 7.39(1H, dd, J=2.0, 8.8 Hz), 7.44(2H, d, J=8.8 Hz), 7.50(1H, d, J=5.6 Hz), 7.58(1H, d, J=2.0 Hz), 7.81 (2H, d, J=8.8 Hz), 8.24 (1H, d, J=5.6 Hz), 8.25 (1H, d, J=8.8 Hz). FAB-MS: 353. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate A6: (3S)-1-(4-Chloro-benzenesulfonyl)-piperidine-3-carboxylic acid (3S)-1-(4-Chloro-benzenesulfonyl)-piperidine-3-carboxylic acid was prepared from 4-chlorobenzenesulfonyl chloride and (S)-(-)-nipecotic acid ethyl ester (available from Aldrich Chemical Company, Inc., Milwaukee, Wisc.) using the procedure described for the preparation of Intermediate A1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In water; | Example 20 4-Chloro-N-(5-chloroquinolin-2-yl)-benzenesulfonamide Pyridine (1 ml) and 4-chlorobenzenesulfonyl chloride (255 mg) were added to <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (119 mg, Preparation Example 2) at room temperature. After stirring at room temperature for 3 days, water was added thereto and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated. Then, the resulting solid was washed with methanol, to give the title compound (20 mg). 1H-NMR (CDCl3) delta (ppm): 6.96 (1H, d, J=9.7 Hz), 7.34 (1H, d, J=8.4 Hz), 7.42-7.48 (3H, m), 7.54 (1H, t, J=8.4 Hz), 7.94 (2H, d, J=6.3 Hz), 8.29 (1H, d, J=9.7 Hz). | |
With pyridine; In water; | Synthetic Example 20b 4-Chloro-N-(5-chloroquinoline-2-yl)-benzenesulfonamide Pyridine (1 ml) and 4-chlorobenzenesulfonyl chloride (255 mg) were added to <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (119 mg, Production Example 2b) at room temperature, followed by stirring at room temperature for 3 days. Then, water was added thereto, followed by extracting with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated. Then, theresulting solid was washed with methanol, to give the title compound (20 mg). 1H-NMR(CDCl3) delta(ppm): 6.96(1H,d,J=9.7Hz), 7.34(1H,d,J=8.4Hz), 7.42-7.48(3H,m), 7.54(1H,t,J=8.4Hz),7.94(2H,d,J=6.3Hz), 8.29(1H,d,J=9.7Hz). | |
With pyridine; In water; | SYNTHETIC EXAMPLE 20b 4-Chloro-N-(5-chloroquinoline-2-yl)-benzenesulfonamide Pyridine (1 ml) and 4-chlorobenzenesulfonyl chloride (255 mg) were added to <strong>[68050-37-3]2-amino-5-chloroquinoline</strong> (119mg, Production Example 2b) at room temperature, followed by stirring at room temperature for 3 days. Then, water was added thereto, followed by extracting with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated. Then, the resulting solid was washed with methanol, to give the title compound (20 mg). 1H-NMR(CDCl3) delta (ppm): 6.96(1H, d, J=9.7 Hz), 7.34(1H, d, J=8.4 Hz), 7.42-7.48(3H, m), 7.54(1H, t, J=8.4 Hz),7.94(2H, d, J=6.3 Hz), 8.29(1H, d, J=9.7 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In tetrahydrofuran; water; ethyl acetate; | Example 164 Preparation of (RS)-2-(4-chlorobenzenesulfonylamino)-4-butanolide (RS)-2-amino-4-hydroxybutanoic acid (2.0438 g) was dissolved in water (20 ml). The solution was cooled to 0° C., and potassium carbonate (5.217 g) and ethyl acetate (20 ml) were added. Then, p-chlorobenzenesulfonyl chloride (9.0536 g) and THF (2 ml) were added, and the whole was stirred overnight. After the reaction was completed, the ethyl acetate layer was separated. The aqueous layer was acidified with 2N HCl and extracted with ethyl acetate. The combined ethyl acetate layers were concentrated to give a crude product. The crude product was purified by silica gel column chromatography (silica gel 50 g, hexane/ethyl acetate=2/1) to obtain (RS)-2-(4-chlorobenzenesulfonylamino)-4-butanolide (2.8674 g). Melting point: 113°-115° C. IR numax cm-1 (KBr): 3255, 1776, 1407, 1336, 1188, 1169, 1091, 756 1 H-NMR delta ppm (CD3 OD): 2.0-2.2 (1H, m), 2.4-2.5 (2H, m), 4.1-4.3 (1H, m), 4.2-4.4 (2H, m), 7.561 (2H, d, J=8.8 Hz), 7.897 (2H, d, J=8.8 Hz) 13 C-NMR delta ppm (CD3 OD): 31.73, 53.22, 67.12, 130.05, 130.60, 140.24, 141.52, 176.58 Fab-MS m/z: 276 (MH+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; potassium iodide; potassium carbonate;aqueous potassium carbonate; In diethyl ether; ethanol; water; butanone; | EXAMPLE 15 2-{4-[2-(4-Chlorobenzenesulphonylamino)-ethyl]-phenoxy}-n-hexanoic acid. A mixture of 17.92 g. (0.1 mol) 4-(2-acetamino-ethyl)-phenol, 17.3 g. (0.125 mol) pulverized potassium carbonate and 150 ml. butan-2-one is stirred for 2 hours at reflux temperature, then 27.9 g. (0.125 mol) ethyl 2-bromohexanoate and a spatula tip of potassium iodide are added thereto and the reaction mixture kept at reflux temperature for a further 28 hours. The reaction mixture is then filtered with suction and the filtrate evaporated in a vacuum. The residue is taken up in diethyl ether and the ethereal phase is extracted with 2 N hydrochloric acid, water, 0.5 N aqueous sodium hydroxide solution and again with water, dried over anhydrous sodium sulphate and evaporated to give 32.1 g. (quantitative yield) ethyl 2-[4-(2-acetaminoethyl)-phenoxy]-n-hexanoate in the form of a colorless oil with a refractive index nD20 =1.5010. A mixture of 25.7 g. (80 mMol) ethyl 2-[4-(2-acetaminoethyl)-phenoxy]-n-hexanoate, 150 ml. water, 150 ml. ethanol and 44.9 g. (0.8 mol) potassium hydroxide is kept at reflux temperature for 16 hours and the alcohol subsequently distilled off in a vacuum. After the addition of 150 ml. water, the reaction mixture is acidified to pH 4 with hydrochloric acid and the resultant precipitate is filtered off with suction, washed with water and dried. There are obtained 12.5 g. (62% of theory) 2-[4-(2-aminoethyl)-phenoxy]-n-hexanoic acid; m.p. 274-276 C. By the reaction of 2-[4-(2-aminoethyl)-phenoxy]-n-hexanoic acid with 4-chlorobenzenesulphonyl chloride in the presence of aqueous potassium carbonate solution, in a manner analogous to that described in Example 1, there is obtained a yield of 32% of theory of 2-{4-[2-(4-chlorobenzenesulphonylamino)-ethyl]-phenoxy}-n-hexanoic acid; m.p. 138-139 C. (recrystallized from ethyl acetate and cyclohexane). |
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 |
---|---|---|
With pyridine; at 80℃; for 0.166667h; | 2-Amino-4-(trifluoromethyl)benzoate (1.86 g, 8.5 mmol) was dissolved in pyridine (12 mL) and 4-chlorobenzenesulfonyl chloride (1.79 g, 8.5 mmol) was added. The resulting solution was heated to 80 0C in a microwave reactor for 10 minutes and then concentrated to dryness. The crude product was purified by column chromatography on silica gel. The column was eluted with 0% to 30% ethyl acetate in cyclohexane to afford methyl 2-[(4-chlorophenyl)sulfonyl]amino}-4-(trifluoromethyl)benzoate as a colourless oil (905 mg). HPLC Rt = 3.63 minutes; m/z [M+H]+ = 394. 1H NMR (CD3OD) delta 8.10 (d, 1 H), 7.91 (S, 1 H), 7.77 (d, 2H), 7.53 (d, 2H)1 7.44 (d, 1 H), 3.90 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In chloroform; at 20℃; for 5h; | A solution of <strong>[37585-16-3](2-amino-4-chlorophenyl)methanol</strong> (5.00 g, 31.85 mmol) and pyridine (3.1 mL) in anhydrous chloroform (150 mL) was treated dropwise with a solution of 4- chlorobenzenesulfonyl chloride (7.26g ,34.58 mmol) in chloroform (30 mL) over 20 minutes at room temperature. The reaction mixture was stirred for 5 hours and evaporated to dryness. The resulting residue was taken up in ethyl acetate (200 mL) and aqueous ammonium chloride (100 mL). After stirring for 30 minutes the organic phase was separated and further washed with dilute ammonium chloride (2 x 50 mL), dried EPO <DP n="29"/>over sodium sulfate, filtered and evaporated to give an oil. This was triturated in hot hexane (10OmL) and then stirred at ambient temperature for 2 hours. The solid was collected and washed with hexane to give the title compound (10.0 g). HPLC Rt = 3.04 minutes. 1H NMR (CDCI3) delta 7.75 (d, 2H), 7.53 (s, 1H), 7.45 (d, 2H), 7.09 (dd, 1 H), 7.01 (d, 1 H), 4.40 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine; | 4-Chloro-N-{6-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indol-4-yl}-benzenesulfonamide. Substituting N-(6-bromo-1H-indol-4-yl)-4-chloro-benzenesulfonamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> with 4-chloro-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=264-266 C, (M+H)+=508. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; | 4-Chloro-N-{6-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indol-4-yl}-benzenesulfonamide. Substituting N-(6-bromo-1H-indol-4-yl)-4-chloro-benzenesulfonamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> with 4-chloro-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=264-266 C, (M+H)+=508. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 1; A mixture of commercially available DL-<strong>[13078-04-1]anabasine</strong> (64.9 mg; 0.4 mmol) and pyridine (252 ul; 3.2 mmol) was stirred in CH2Cl2 at 0C for 1 h. 4-chlorobenzenesulfonylchloride (126.6 mg; 0.6 mmol) was added and subsequently stirred at 10C for 18 h. The crude reaction mixture was then purified on a Varian reverse-phase preparative HPLC to afford the product example 1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium hydride; In tetrahydrofuran; at 0℃; for 6h; | General procedure: The target compound 7a was obtained by reacting 4a (295 mg, 1.0 mmol) with benzenesulphonyl chloride (211 mg, 1.2 mmol), and NaH (50 mg, 2.0 mmol) in dry THF (50 mL). After stirring the reaction mixture for 6 h, the reaction mixture was poured on to crushed ice (5 g) and the reaction mixture extracted and purified by column chromatography affords final product as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Embodiment 4: Preparation of Compound 5d (4-Chloro-N-(1H-indol-7-yl)benzenesulfonamide); The compound 4 of the Embodiment 1 (2.48 g, 15.30 mmol) was dissolved in isopropanol (45 mL), and then Fe powder (2.56 g, 45.8 mmol) and an NH4Cl solution formulated with NH4Cl (0.16 g, 9 mmol) and water (9 mL) were added. After the resulting solution was heated at 60 C for 2 hr, a TLC test was used to confirm the completion of the reaction. Then, active charcoal was added into the reaction solution, and stirred for 3 min. The solution was filtered, and ethyl acetate was used to wash the residue until the volumn of the filtrate was 150 mL. A solution formulated with 4-chlorobenzenesulfonyl chloride (3.38 g, 16.00 mmol) and pyridine (3.70 mL, 45.97 mmol) was added into the solution. The resulting solution was stirred at room temperature for 7.5 hr, and a TLC test was used to confirm the completion of the reaction. After the reaction was completed, ethyl acetate was added to dilute the reaction solution to 250 mL. Then, the reaction solution was sequentially washed with 1 N of HCl, water, saturated NaHCO3 solution, and brine. The color of the organic layer was red oxide after the washing steps. Na2SO4 was added for dehydration, and the organic layer was filtered and concentrated to obtain a solid. The solid was re-crystallized in ethanol to obtain a plate-shaped yellow solid, compound 5d (3.13 g, 67%). mp 163-164 C (lit. 163-164.5 C); 1H NMR (200 MHz, CDCl3) delta6.44 (d, J= 7.4 Hz, 1H, ArH), 6.54 (dd, J= 2.2 , 3.0 Hz , 1H, ArH), 6.84 (t, J = 7.6 Hz, 1H, ArH), 6.96 (s, 1H, NH), 7.34-7.41 (m, 2H, ArH), 7.46-7.55 (m, 2H, ArH), 7.64-7.69 (m, 2H, ArH), 9.28 (s, 1H, NH); 13C NMR (50 MHz, CDCl3) delta103.2, 118.7, 119.8, 120.2, 120.7, 125.8, 129.3, 129.7, 130.7, 132.3, 136.6, 140.2; MS (EI) m/z 306 (M+, 25%), 131 (M-171, 90%), 104 (M-182, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In tetrahydrofuran; for 16h; | A mixture of 4-chlorobenzene-l-sulfonyl chloride (3.82 g, 18.12 mmol), (2S,3S)- 2-aminobutane-l ,3-diol (<strong>[44520-55-0]D-threoninol</strong>, 2.0g, 19.02 mmol) and potassium carbonate in anhydrous THF (20 mL) was stirred for 16 h. THF was removed in vacuo and the residue was partitioned between water (20 mL) and ethyl acetate (30 mL). The organic layer was separated and washed with 2N HCl, water, 10 % sodium bicarbonate solution, water, brine and dried. Filtration and removal of solvent provided 4.30 g of final product.MS (m/z): 280.42 (M++l) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In tetrahydrofuran; for 16h; | A mixture of 4-chlorobenzene-l-sulfonyl chloride (3.82 g, 18.12 mmol), (2R,3R)- 2-aminobutane-l,3-diol (<strong>[3228-51-1]L-threoninol</strong>, 2.0g, 19.02 mmol) and potassium carbonate (6.26 g, 45.3 mmol) in anhydrous THF (20 mL) was stirred for 16 h. THF was removed in vacuo and the residue was partitioned between water (20 mL) and ethyl acetate (30 mL). The organic layer was separated and washed with 2N HC1, water, 10 % sodium bicarbonate solution, water, brine and dried. Filtration and removal of solvent provided 3.99 g of product.MS (m/z): 280.62 (M++l) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.8% | To a solution of (.pound.)-(+)- phenyl-glycinol (1.0 g, 7.3 mmol) in dichloromethane (30 mL) was added triethyl amine (2.89 ml, 20.8 mmol). The mixture was then added to 4-chloro-phenylsulfonayl chloride (1.46 g, 6.9 mmol), stirred at room temperature for 16 h, followed by acidification with 2 N HC1 to pH 3. The organic layer was separated and washed with water, aqueous sodium bicarbonate, water, brine and dried over sodium sulfate. Filtration and concentration provided 1.69 g of solid crude product that was triturated with diethyl ether to yield 1.31 g (60.8percent) of white solid.MS: (m/z) 312.14 (M++l) |
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 |
---|---|---|
98.7% | With bis(benzonitrile)palladium(II) dichloride; tributylphosphine; 25,26,27,28-tetrakis(hydroxy)calix[4]arene; sodium carbonate; In 1,4-dioxane; at 90℃; for 24h;Inert atmosphere; | Added to the synthesis reactor 1mmol formula (I) compounds and 1.8mmol compound of formula (II), then adding 5 ml solvent 1,4-dioxane and 8mmol sodium carbonate, stirring, add 0.09mmolPd (PhCN)2Cl 2 and 75 mg mass ratio of 1 : 0.8 cup [4] arenes and tributylphosphine additive mixture, and then carry on argon-vacuum suction replacement three times, and then sealing the stirring and gradually raising the temperature to 90 C reaction 24h, after the reaction cooled to room temperature, mixed solution by filtration, after the spin vaporization, the silica gel column chromatography purification, the compounds of formula (III) can be obtained, the yield of 98.7%, purity of 98.5% (HPLC) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With pyridine; In tetrahydrofuran; at 0℃; for 4h; | To a solution of <strong>[58196-33-1]1,2,3,4-tetrahydroquinolin-7-ol</strong> (4.68g, 31.4mmol, Astatech) and pyridine (3.04mL, 37.6mmol) in THF (30mL) at 0C was added a solution of 4-chlorobenzene-1-sulfonyl chloride (6.95g, 32.9mmol) in THF (15mL) dropwise. The reaction was stirred at 0C for 4h. The reaction mixture was concentrated with silica gel and purified by flash chromatography (10-40% EtOAc in hexanes) to give 49 (8.8g, 87%) as a pale-yellow solid. 1H NMR (400MHz, chloroform-d) delta ppm 7.54-7.58 (2H, m), 7.37-7.41 (2H, m), 7.36 (1H, d, J=2.5Hz), 6.89 (1H, d, J=8.4Hz), 6.64 (1H, dd, J=8.4, 2.5Hz), 3.76-3.82 (2H, m), 2.40 (2H, t, J=6.7Hz), 1.57-1.65 (2H, m). MS ESI (pos.) M/E: 324 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With triethylamine; In dichloromethane; for 4h;Reflux; | Synthesis of methyl 1-[(4-chlorophenyl)sulfonylamino]cyclopropanecarboxylate 13B To <strong>[72784-42-0]methyl 1-aminocyclopropanecarboxylate hydrochloride</strong> 12 (500 mg, 3.298 mmol) dissolved in methylene chloride (20ml) was added with TEA (2 equiv., 1 ml) and in one portion 4-chlorobenzenesulfonyl chloride (1.0 equiv., 765 mg). The reaction was refluxed for 4 hours. The solvent was evaporated and the crude was dissolved in EtOAc (50 ml) and washed with water (1 X 30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by crystallization from diethyl ether and petroleum ether afforded 800 mg of the white product 13B. Yield = 84percent 1HNMR (DMSO, 200 MHz) delta 1.16 (2H, m), 1.30 (2H, m), 3.32 (3H, s), 7.70 (4H, m), 8.87 (1H, bs) |
84% | With triethylamine; In dichloromethane; for 4h;Reflux; | Synthesis of methyl l-[(4- chlorophenyl)sulfonylamino]cyclopropanecarboxylate 13B To <strong>[72784-42-0]methyl 1-aminocyclopropanecarboxylate hydrochloride</strong> 12 (500 mg, 3.298 mmol) dissolved in methylene chloride (20ml) was added with TEA (2 equiv., 1 ml) and in one portion 4-chlorobenzenesulfonyl chloride (1.0 equiv., 765 mg). The reaction was refluxed for 4 hours. The solvent was evaporated and the crude was dissolved in EtOAc (50 ml) and washed with water (1 X 30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by crystallization from diethyl ether and petroleum ether afforded 800 mg of the white product 13B. Yield = 84percent FontWeight="Bold" FontSize="10" HNMR (DMSO, 200 MHz) delta 1.16 (2H, m), 1.30 (2H, m), 3.32 (3H, s), 7.70 (4H, m), 8.87 (1H, bs) |
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 |
---|---|---|
67% | With tetrabutylammomium bromide; sodium hydroxide; In benzene; at 0 - 20℃; | General procedure: To a solution of 1,7'-dimethyl-2'-propyl-1H,3'H-2,5'-bibenzo[d]imidazole 3 (2 mmol) and tetrabutylammonium bromide (0.2 mmol) in benzene (25 mL), a solution of 50% NaOH (25 mL) was added at 0 C followed by the addition of sulfonyl chloride 4 (2.2 mmol). The reaction mixture was stirred vigorously at room temperature for 5-6 h and the reaction was monitored by TLC. After the completion of the reaction, aqueous phase was separated and the organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate and concentrated to give crude products which were purified by column chromatography over silica gel using hexane-EtOAc (6:4) mixture as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With pyridine; In tetrahydrofuran; at 60 - 65℃; for 0.25h;Microwave irradiation; | General procedure: To a solution of <strong>[92914-74-4]3-aminoisoxazolo[5,4-b]pyridine</strong>(1) (1.35 g, 0.01 mol) in 100 mL of tetrahydrofurane tetrahydrofurane,a few drops of anhydrous pyridine and 0.01mol of the appropriate arylsulfonyl chlorides: benzene-,4-bromobenzene-, 4-chlorobenzene-, ptoluene-and 4-methoxybenzenesulfonyl chlorideswere added. The reaction mixture was heated underreflux while being stirred in the microwave reactorin an aluminum bath at 60-65OC for 15 min (3 5min with 5 min breaks) at microwave power P = 240W. The solvent was evaporated under vacuum andthe residue obtained was triturated with water, filtered,dried and crystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With pyridine; In tetrahydrofuran; at 60 - 65℃; for 0.25h;Microwave irradiation; | General procedure: To a solution of <strong>[92914-74-4]3-aminoisoxazolo[5,4-b]pyridine</strong>(1) (1.35 g, 0.01 mol) in 100 mL of tetrahydrofurane,a few drops of anhydrous pyridine and 0.02mol of the appropriate arylsulfonyl chlorides: benzene-,4-bromobenzene-, 4-chlorobenzene- and 4-methylbenzenesulfonyl chlorides were added. Thereaction mixture was heated under reflux whilebeing stirred in the microwave reactor in an aluminumbath at 60-65OC for 15 min (3 5 min with5 min breaks) at microwave power P = 240 W. Thesolvent was evaporated under vacuum and theresidue obtained was triturated with water, filtered,dried and recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.63% | With pyridine; at 90℃; | A mixture of la (0.35 g, 1.76 mmol), 4-chlorobenzenesulfonyl chloride (0.56 g, 2.64 mmol), and pyridine (3ml) was refluxed overnight. The reaction was quenched with water and the mixture was extracted with ethyl acetate (30 ml x 3). The organic layer was collected, dried over anhydrous MgS04, and concentrated in vacuo to yield a brown residue, which was purified by a flash column over silica gel (ethyl acetate: n-hexane = 1: 1, Rf = 0.78) to afford 2g (0.55 g, 83.63%) as a yellow solid. *H-NMR (500MHz, CDC13): delta 3.06 (t, /= 8.5 Hz, 2H), 4.08 (t, /= 8.5 Hz, 2H), 7.46-7.47 (m, 3H), 8.03 (d, /= 9.0 Hz, 2H), 8.17 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With water; sodium carbonate; | General procedure: Aqueous sodium carbonate solution (3-5%) containing A-1 (286 mg, 0.7 mmol) was treated with equimolar ratio of 4-chlorobenzenesulfonyl chloride, 4-chlorobenzoyl chloride,and 2,5-dichlorobenzenesulfonyl chloride separatelyfor 3-6 h. The execution and completion of reactions were indicated by thin-layer chromatography. White precipitates were formed by adding 3 N HCl dropwise up to 2.0 pH. The products were filtered and recrystallized in MeOH/EtOAc (50:50 v/v) to obtain colorless blocks 2-[2-(4-Chloro-benzenesulfonylamino)-ethoxymethyl]-4-(2-chloro-phenyl)-5-hydroperoxycarbonyl-6-methyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester dehydrate (A-2) Yield: 67%, mp 148-150 C, 1H NMR (400 MHz, CDCl3, d,ppm): 7.9 (d, J 8.1 Hz, 2H, H-23, H-25), 7.5 (d, J 8.1 Hz,2H, H-22, H-26), 7.4e7.1 (m, 4H, H-2eH-6), 5.4 (s, 1H, H-7),4.9 (s, 2H, H-18), 4.07 (m, 2H, H-16), 3.7 (m, 2H, H-19), 3.6(s, 3H, H-13), 3.2 (m, 2H, H-20), 2.3 (s, 3H, H-14), 1.2 (t, 3H,H-17). IR (KBr) numax (cm1) 3377 (NeH stretch), 3267 (sec.sulfonamide), 1686, 1662 (C]O stretch), 1645, 1603 (C]Cstretch), 1480, 1429 (aliphatic CeH, bending), 1281 (S]O,asymmetric stretch), 1202 (O]CeO ester, stretching), 1186(OeCeC of ester, stretching), 1082 (S]O symmetricstretch), 1035 (aromatic CeCl), 757, 737 (aromatic CeH,bending). MS m/z (%): 618 (2, M), 585 (45), 583 (100), 581(94), 318 (6), 286 (8). Anal. Calcd for C26H32Cl2N2O9S (619.51): C, 50.41; H, 5.21; N, 4.52; S, 5.18. Found: C, 50.24;H, 5.33; N, 4.60; S, 5.43% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With pyridine; In dichloromethane; at 20℃; for 18h; | General procedure: To a stirring mixture of 5-amino-2-(4-aminophenyl) benzoxazole (1 eq.) in anhydrous CH2Cl2 (5 mL) was added the respective sulfonyl chloride (2.1 eq.) followed by anhydrous pyridine (2.1 eq.). The reaction was allowed to stir at room temperature for 18 h and was then chromatographed over silica and concentrated. If necessary, the product was further purified by preparatory RP-HPLC (H2O:CH3CN gradient), concentrated, and lyophilized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With triethylamine; In tetrahydrofuran; at 20℃; for 4h; | General procedure: Coumarin sulfonates 1-38 were synthesized by reactingdifferent hydroxylated coumarin derivatives (1 mmol) withcommercially available sulfonyl chlorides derivatives (1.2 mmol) inTHF (15 mL) and triethyl amine (1 mmol) was used as base. Reactionmixture was stirred for 4 h at room temperature to afford avariety of coumarin sulfonate esters 1e38. TLC monitoring wasused to determine the progress of the reaction. After the completionof reaction, THF was evaporated under reduced pressure andthe solid product obtained was washed with distilled water anddried under vacuum. The products were recrystallized in methanoland gave good yields. All the synthetic compounds 1-38 werecharacterized by different spectroscopic techniques such as EI-MS,HREI-MS, 1H-NMR, and 13C-NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 20℃; | (R) - [3- (3-fluoro-4-morpholinophenyl) -2-oxo-5-oxazolidinyl] methyl alcohol(3.9 g, 13.16 mmol) and CH2Cl2,Stirred and then triethylamine (3.67 mL, 26.13 mmol) was added.A solution of p-chlorobenzenesulfonyl chloride (15.8 mmol) in CH2Cl2 was added dropwise and reacted at room temperature overnight.TLC monitoring, the reaction is completed, the reaction solution water washing, saturated NaCl solution washing,Dried over anhydrous Na2SO4, filtered, dried to give the crude product,The crystals were recrystallized to give a pale yellow powder(R) -N- [3- (3-fluoro-4-morpholinophenyl) -2-oxo-5-oxazolidinyl] methyl p-chlorobenzenesulfonic acidEster 5.4 g,Yield: 87.2%, chemical purity: 98.7% |
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 |
---|---|---|
72% | With triethylamine; In tetrahydrofuran;Heating; | General procedure: To a stirred solution of 4-chlorobenzenesulfonyl chloride (1) (0.001 mol) in dry THF, 2-(phenylthio)aniline (3a) (0.001mol) was added at 20C in the presence of triethylamine (0.001 mol) as a base in THF (20 mL). After the addition, the reaction mixture temperature was slowly raised to 40-50C and stirred for 4 h. The progress of the reaction was monitored by TLC using ethyl acetate: hexane (3:2). After completion of the reaction, the triethylamine hydrochloride salt was fltered off and the solvent was removed in a rotaevaporator. The residue was purifed by washing with hexane and recrystallization from ethanol. The resulting compound 4-chloro-N-(2-(phenylthio)phenyl)benzenesulfonamide (4a) was obtained in good yield (75%). The same procedure was adopted for the synthesis of the remaining title compounds (4b-f). The title compounds (5a-f) were synthesized by adopting the above procedure using 4-uorobenzenesulfonyl chloride (1) with the same amines (3a-f) (Scheme 1). |
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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.8% | With triethylamine; In tetrahydrofuran;Heating; | Compound 10 (50·0 g, 144 mmol), TEA (51.1 g, 505 mmol), p-chlorobenzenesulfonyl chloride 2 (54.9 g, 260 mmol) and tetrahydrofuran (500 mL).Heating and stirring; Water (5000 mL) was added, the temperature was lowered, filtered and dried to give BMS-708163 (68.3 g, 90.8%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With triethylamine; In methanol; at 20℃; | General procedure: Solutions of selected methyl ketones (2 mmol) in methanol(6 mL) were stirred and corresponding sulfonylchlorides (2.4 mmol) were added. Then, triethylamine(0.6 mL) was added dropwise. The mixtures were stirredovernight at room temperature. After completion of thereactions, mixtures were poured into iced water withstirring. In some cases (for our compounds 7f, 7g, 8e, 8f,8g, and 9g; see below), the formed precipitate was filteredand washed with cold diethyl ether. In other cases, whenno precipitate formed, the organic layer was extractedwith dichloromethane (3 × 50 mL), dried over anhydrousNa2SO4 and evaporated under vacuum. The residue waspurified by short column chromatography on silica gel,using dichloromethane as eluent. The oil obtained usuallycrystallized; if not, the oily residue was dissolved indiethyl ether from which products crystallized on standingin a deepfreeze. Crude products were washed with coldether, and 21 pure, mostly white crystals were obtained, asfollows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20℃; for 25h; | General procedure: <strong>[3366-95-8]Secnidazole</strong> (1 mmol) was dissolved in dioxane (6 mL) on icebath.After complete dissolution, we slowly added substitutedsulphonylchloride (1a-9a) (2 mmol). After 30 min, 33% aqueousNaOH (aq) solution (5 mL) was added to the reaction mixture withcontinuous stirring for 1 h. The ice bath was removed and stirringcontinued for 24 h at room temperature then reaction mixture waspoured onto ice-water, precipitates were obtained and recrystallizedwith minimum diethyl ether to obtain pure products (M1-M9). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With triethylamine; In dichloromethane; at 25℃; for 8.0h; | General procedure: An equimolar mixture of N-(2,6-dimethy lphenyl)-2-(piperazin-1-yl)acetamide 4 (0.001 mol) and different substituted benzene sulfonyl chlorides 5a-e (0.001 mol) in methylene dichloride were stirred for about 8 h in presence of triethylamine at 25oC. The completion of the reaction was checked by TLC. Then it was poured into ice-cold water and extracted with MDC. The organic layer was washed with brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to get piperazine sulphonamide derivatives 6a-e in high yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.77% | With dmap; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 5℃; for 2h; | Add III-4 (0.50g, 3.14mmol), DMAP (77mg, 0.63mmol), DIEA (1.56mL, 9.42mmol) to 100mL three-necked flask, stir and dissolve with 10mL acetonitrile, slowly add at 05C 4-Chlorophenylsulfonyl chloride (IV-5, 0.80 g, 3.77 mmol) in 10 mL of acetonitrile solution, after the addition was completed, stirring was continued for 2 h under low temperature conditions.TLC monitoring the raw material reaction is complete,The reaction solution was concentrated, dissolved with ethyl acetate (30 mL), 40 mL of waterThe phase was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate; suction filtered, and the filtrate was dried and then subjected to column chromatography ( petroleum ether: acetic acidEster = 10:1 rinse),After drying, 0.72 g of a brownish yellow solid V-12 was obtained with a yield of 68.77%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With Schwartz's reagent; In tetrahydrofuran; at 20 - 60℃; for 18h; | The compound 4-chlorobenzenesulfonyl chloride was combined with /er/-butyl but-3- yn-l-yl carbamate, Cp2Zr(H)Cl (1.2 eqv.), and tetrahydrofuran, and the mixture stirred from room temperature to 60 C for 18 h to produce tert-butyl (E)-(4-((4- chlorophenyl)sulfonyl)but-3-en-l-yl)carbamate. |
Tags: 98-60-2 synthesis path| 98-60-2 SDS| 98-60-2 COA| 98-60-2 purity| 98-60-2 application| 98-60-2 NMR| 98-60-2 COA| 98-60-2 structure
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P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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