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CAS No. : | 32857-48-0 | MDL No. : | MFCD00444460 |
Formula : | C13H12BrNO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RIBFVUXANOZLHJ-UHFFFAOYSA-N |
M.W : | 326.21 | Pubchem ID : | 182097 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P270-P301+P312-P330-P501 | UN#: | |
Hazard Statements: | H302 | Packing Group: | |
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 pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With pyridine In dichloromethane for 2h; Inert atmosphere; | |
100% | With triethylamine In dichloromethane at 4℃; | |
99% | With pyridine In dichloromethane at 20℃; for 16h; |
96% | With (Na1752K0.144Ca0365Mg0.065)(Al2044Si2774O96)*19.16H2O In ethanol at 25 - 30℃; for 0.333333h; Sonication; Green chemistry; | 3.3 General procedure for the N-sulfonylation of amines by Natrolite nanozeolite under ultrasound irradiation General procedure: The reactions were carried out in a round-bottomed flask of 25mL capacity suspended at the center of the cleaning bath, 5cm below the surface of the liquid. To the mixture of amine (1.0mmol) and tosyl chloride (1.0mmol) in 4mL of ethanol, Natrolite nanozeolite (0.08g) was added. The mixture was sonicated at 25-30°C (bath temperature, the temperature inside the reactor was also 25-30°C) for the appropriate time (Table 5) in an US bath having a frequency of 40kHz and an input power of 250W. The addition or removal of water controlled the temperature of the water bath. The water bath was controlled at 25-30°C. The progress of the reaction was monitored by TLC. After completion of the reaction, catalyst was filtrated. The filtrated catalyst, which was washed with ethyl acetate and activated at 100°C for 2h, could be reused in next cycle without considerable activity loss at least five successive runs for the same reaction. The solvent was concentrated under reduced pressure to afford the pure product as solid in good to excellent yields. All compounds were compared with the corresponding compounds prepared by the reported procedure [7,24-28]. All compounds were known and were characterized by spectral analysis. |
96% | With pyridine at 0 - 25℃; Inert atmosphere; Schlenk technique; | |
96% | With pyridine In dichloromethane at 0 - 20℃; for 3.5h; | |
95% | In water at 20℃; for 0.416667h; | |
95% | With pyridine for 4h; Reflux; | |
93% | With caesium carbonate In acetonitrile at 25℃; for 0.416667h; | |
93% | With dendritic fibrous nanosilica KCC-1 3-aminopropyl-functionalized supported on Fe3O4 magnetic nanocatalyst In water at 20℃; for 0.666667h; Green chemistry; | |
88% | at 20℃; for 0.166667h; | |
87% | With pyridine at 0 - 25℃; | |
86% | With copper(II) oxide In acetonitrile at 20℃; for 1.5h; | |
86% | With cadmium(II) oxide In acetonitrile for 0.416667h; Reflux; | |
84% | In acetonitrile at 20℃; for 8h; | |
81% | With silica-supported ferrocene-tagged ionic liquid phase catalyst containing Keggin-type anion In dichloromethane at 20℃; for 0.833333h; Green chemistry; | |
79% | With pyridine for 4h; Heating; | |
78% | With pyridine In dichloromethane at 20℃; for 2h; Inert atmosphere; Schlenk technique; | |
62% | With triethylamine In acetone at 20℃; Cooling with ice; | |
20% | With triethylamine In dichloromethane at 0 - 20℃; | |
With pyridine; diethyl ether | ||
With pyridine In dichloromethane at 20℃; | ||
With pyridine for 0.0833333h; Heating; | ||
With pyridine In dichloromethane for 16h; | ||
With pyridine at 20℃; | ||
Alkaline conditions; Inert atmosphere; | ||
In pyridine at 20℃; for 2h; | ||
With pyridine In dichloromethane at 40℃; for 1h; | Derivatization General procedure: Tosylation of haloanilines was carried out by the classical method (Scheme 1).23 Each haloaniline was mixed with p-toluenesulfonyl chloride in dichloromethane in the presence of pyridine, and the resulting mixture was kept at 40C for 60 min. The solvent was removed by reduced pressure distillation, and the residue was purified by silica gel chromatography. The purity of the corresponding derivative products was determined by HPLC (see the supplementary Figure S3). | |
With pyridine In dichloromethane at 20℃; for 15h; Inert atmosphere; | N-Allenyl-N-(4-bromophenyl)-4-p-toluenesulfonamide (1i) A modified procedure was applied for this synthesis. A two-neck flask of suitable size equipped with a magnetic stirrer and a gas inlet tube was conditioned under Ar and charged with 4-bromoaniline (1.0 equiv). Dry DCM (6 mL per mmol of substrate) was then added, followed by TsCl (1.1 eq) and pyridine (3.0 eq). The mixture was stirred for 15 h at room temperature, then quenched with NH4Cl and transferred to a separatory funnel. After extraction with DCM, the organic phase was washed with HCl (1M in H2O) and brine. Exsiccation over MgSO4 and evaporation of the solvent gave the required N-4-bromophenyl-p-toluenesulfonamide, which was employed for the next step without purification. A solution of the obtained compound in acetone (0.50 M) under argon was stirred with K2CO3 (2 equiv) for 10 min and propargyl bromide (80% solution in toluene, approx. 9.2 M, 1.2 equiv) was added. After one night at room temperature, the mixture was filtered and concentrated in vacuo. Then EtOAc was added to the residue and this organic layer was washed with NaOH (half volume, three times) and brine. The crude product obtained after drying over MgSO4 and concentration under reduced pressure was directly engaged into the isomerization according to the general procedure B (reaction time: 12 h) to give the title compound in 54% yield over three steps. | |
With triethylamine In tetrahydrofuran for 6h; Reflux; | ||
With triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine at 150℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With Oxone; sodium nitrite In nitromethane at 50℃; chemoselective reaction; | |
89% | With sulfuric acid; sodium nitrite In acetic acid for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium carbonate In acetonitrile for 9h; Reflux; | |
86% | Stage #1: N-(4-bromophenyl)-4-methylbenzenesulfonamide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: dimethyl sulfate In N,N-dimethyl-formamide at 20℃; for 24h; | |
82% | With potassium hydroxide In water 1) 40 degC, 15 min, 2) reflux, 10 min; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With nickel dibromide In benzonitrile for 4h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With n-butyllithium; Trimethyl borate; bromine In tetrahydrofuran at -78 - 0℃; | |
75% | With bis-[(trifluoroacetoxy)iodo]benzene; sodium bromide In ethanol at 25℃; for 7h; Green chemistry; regioselective reaction; | |
71% | With Eosin Y; Selectfluor In acetonitrile at 25℃; for 6h; regioselective reaction; |
With N-Bromosuccinimide; chloro-trimethyl-silane In acetonitrile at 20℃; for 1h; | General procedure for the electrophilic aromatic halogenation. 4-bromo-2-chloro-1-methoxybenzene (2a-Cl) and 2,4-dichloro-1-methoxybenzene (2a-diCl) General procedure: To a solution of 4-bromoanisole (200.8 mg, 1.09 mmol, 1.0 equiv) in acetonitrile (2 mL) was added N-chlorosuccinimide(NCS) (158.3 mg, 1.19 mmol, 1.1 equiv) at rt to give a slightly cloudy mixture. Chlorotrimethylsilane (TMSCl) (14 μL, 0.11 mmol, 0.1 equiv) was then added drop-wise to the reaction mixture. Within a few minutes, the reaction mixture became clear pale yellow solution. The mixture continued to stir at rt for 1 h and was diluted with hexane. The biphasic mixture was concentrated on a rotary evaporator to a crude white solid-oil mixture. This mixture was taken up in hexane and filtered through a short plug of SiO2 and eluted with 5-10% EtOAc-hexane solution. The clear filtrate was concentrated to obtain a mixture of 4-bromo-2-chloro-1-methoxybenzene (2a-Cl) and 2,4-dichloro-1-methoxybenzene (2a-diCl) 237.0 mg (88% of 2a-Cl and 11% of 2a-diCl,based on NMR ratio 2a-Cl: 2a-diCl = 7.1: 1.0; as a pale yellow solid). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In tetrahydrofuran for 16h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Et3N / methanol 2: 39 percent / TfOH / CH2Cl2 / 0.33 h / 20 °C 3: KOH / dimethylsulfoxide / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N / methanol 2: 39 percent / TfOH / CH2Cl2 / 0.33 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 46 percent / NiBr2 / benzonitrile / 4 h / Heating 2: 100 percent / aq. NaOH / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 82 percent / KOH / H2O / 1) 40 degC, 15 min, 2) reflux, 10 min 2: 39 percent / n-BuLi / tetrahydrofuran / -105 degC -> room temp. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 82 percent / KOH / H2O / 1) 40 degC, 15 min, 2) reflux, 10 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 82 percent / KOH / H2O / 1) 40 degC, 15 min, 2) reflux, 10 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: N-(4-bromophenyl)-4-methylbenzenesulfonamide With water; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at -10℃; Stage #2: 4-Methoxystyrene In acetonitrile at -10 - 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tetrakis(triphenylphosphine) palladium(0) at 100℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-(4-bromophenyl)-4-methylbenzenesulfonamide With [bis(acetoxy)iodo]benzene In methanol at 25℃; for 0.25h; Stage #2: With indole; copper(ll) bromide In methanol at 25 - 70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 135℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With trifluoroacetic acid for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 4,4'-Dimethoxy-2,2'-bipyridin; NiI2*3.5H2O; sodium iodide; zinc at 20 - 60℃; for 16h; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: N-(4-bromophenyl)-4-methylbenzenesulfonamide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: propargyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 16h; Inert atmosphere; Schlenk technique; | |
With sodium hydride | ||
Stage #1: N-(4-bromophenyl)-4-methylbenzenesulfonamide With potassium carbonate In acetone for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: propargyl bromide In acetone at 20℃; for 5h; Inert atmosphere; Schlenk technique; |
With potassium carbonate In acetone Reflux; Inert atmosphere; | ||
With potassium carbonate In acetonitrile at 80℃; for 8h; | ||
Stage #1: N-(4-bromophenyl)-4-methylbenzenesulfonamide With potassium carbonate In acetone for 0.166667h; Inert atmosphere; Stage #2: propargyl bromide In acetone; toluene at 20℃; Inert atmosphere; | N-Allenyl-N-(4-bromophenyl)-4-p-toluenesulfonamide (1i) A modified procedure was applied for this synthesis. A two-neck flask of suitable size equipped with a magnetic stirrer and a gas inlet tube was conditioned under Ar and charged with 4-bromoaniline (1.0 equiv). Dry DCM (6 mL per mmol of substrate) was then added, followed by TsCl (1.1 eq) and pyridine (3.0 eq). The mixture was stirred for 15 h at room temperature, then quenched with NH4Cl and transferred to a separatory funnel. After extraction with DCM, the organic phase was washed with HCl (1M in H2O) and brine. Exsiccation over MgSO4 and evaporation of the solvent gave the required N-4-bromophenyl-p-toluenesulfonamide, which was employed for the next step without purification. A solution of the obtained compound in acetone (0.50 M) under argon was stirred with K2CO3 (2 equiv) for 10 min and propargyl bromide (80% solution in toluene, approx. 9.2 M, 1.2 equiv) was added. After one night at room temperature, the mixture was filtered and concentrated in vacuo. Then EtOAc was added to the residue and this organic layer was washed with NaOH (half volume, three times) and brine. The crude product obtained after drying over MgSO4 and concentration under reduced pressure was directly engaged into the isomerization according to the general procedure B (reaction time: 12 h) to give the title compound in 54% yield over three steps. | |
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | ||
With potassium carbonate In acetone at 60℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydride 2: n-butyllithium 3: iron(III) chloride; silver trifluoromethanesulfonate / 1,2-dichloro-ethane / 0.33 h / 25 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydride 2: copper dichloride; sodium carbonate; pyridine; oxygen 3: iron(III) chloride; silver trifluoromethanesulfonate / 1,2-dichloro-ethane / 0.17 h / 25 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: copper dichloride; sodium carbonate / 0.25 h 1.2: 0.25 h / 70 °C / 760.05 Torr 1.3: 8 h / 70 °C 2.1: potassium carbonate / methanol / 20 °C 3.1: (triphenylphosphine)gold(I) chloride; silver hexafluoroantimonate; pyridine N-oxide / dichloromethane / 17.25 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: copper dichloride; sodium carbonate / 0.25 h 1.2: 0.25 h / 70 °C / 760.05 Torr 1.3: 8 h / 70 °C 2.1: potassium carbonate / methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-(4-bromophenyl)-4-methylbenzenesulfonamide With sodium carbonate; copper dichloride for 0.25h; Stage #2: With pyridine; oxygen In toluene at 70℃; for 0.25h; Stage #3: trimethylsilylacetylene In toluene at 70℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium carbonate In acetonitrile at 80℃; for 16h; Inert atmosphere; | |
93% | With potassium carbonate In acetone at 65℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 16 h / 80 °C / Inert atmosphere 2: hydrogen fluoride; antimony pentafluoride / 0.17 h / -65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With formic acid; [Au2(μ-bis(diphenylphosphanyl)methane)2][Cl]2; N-ethyl-N,N-diisopropylamine In acetonitrile Inert atmosphere; UV-irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 4,4'-bipyridine; NiI2*3.9H2O; triethylamine hydrochloride; sodium iodide; zinc at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate In water for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium isocyanate / water / 0.17 h / Reflux 2: potassium carbonate / water / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper(l) chloride In methanol at 20℃; for 2h; | |
91% | With L-proline-functionalized MCM-41-immobilized-CuCl; air In methanol at 20℃; for 6h; | |
83% | With Copper(II) immobilized into prolinamide-modified polyacrylonitrile fiber In methanol at 60℃; for 0.5h; |
76% | With air; Graphene supported-1-N-ferrocenylmethylimidazole-Copper complex In ethanol at 70℃; for 0.666667h; | |
63% | With [Cu(4-(dimethylamino)pyridine)4I]I In methanol at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: Ethyl 4-bromobutyrate; N-(4-bromophenyl)-4-methylbenzenesulfonamide With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 4,4'-Dimethoxy-2,2'-bipyridin; nickel(II) iodide hydrate; sodium iodide at 60℃; Inert atmosphere; Stage #2: With zinc at 60℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: caesium carbonate; iodine / acetonitrile / 4 h / 20 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 4 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; caesium carbonate In acetonitrile at 20℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With potassium phosphate; copper(l) chloride In water at 20℃; for 10h; | General procedure for the N-arylation of N-arylsulfonamideswith diaryliodonium salts (Table 2, 3) General procedure: A mixture of N-arylsulfonamide1 (0.2 mmol, 1 equiv.), diaryliodonium salt 2(0.24 mmol, 1.2 equiv.), K3PO4(0.4 mmol, 2 equiv.), CuCl (0.04 mmol, 20 mol%)and H2O (3 mL) was taken in a 10 mLreaction tube at room temperature for 10-16 hunder vigorous stirring. After completion of the reaction, as indicated by TLC,the reaction mixture was concentrated under reduced pressure, and the crudecompound was purified by chromatography on a silica gel column (ethylacetate/petroleum ether (1/15)) to afford the desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0.17 h / Inert atmosphere; Schlenk technique 1.2: 5 h / 20 °C / Inert atmosphere; Schlenk technique 2.1: copper(I) thiophene-2-carboxylate / toluene / 0.05 h / 20 °C / Inert atmosphere; Schlenk technique 2.2: 4 h / 20 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 0.17 h / Inert atmosphere; Schlenk technique 1.2: 5 h / 20 °C / Inert atmosphere; Schlenk technique 2.1: copper(I) thiophene-2-carboxylate / toluene / 0.05 h / 20 °C / Inert atmosphere; Schlenk technique 2.2: 4 h / 20 °C / Inert atmosphere; Schlenk technique 3.1: lithium chloride; rhodium(II) pivalate / 1,2-dichloro-ethane / 3 h / 60 °C / Inert atmosphere; Schlenk technique; Molecular sieve |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichlorotriphenylphosphorane; triethylamine / chloroform / 0.33 h / 0 °C 2: ammonia / chloroform / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; dichlorotriphenylphosphorane In chloroform at 0℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 25℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 12 h / 25 °C 2: dipotassium peroxodisulfate; silver nitrate / acetonitrile; water / 12 h / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 12 h / 25 °C 2: dipotassium peroxodisulfate; silver nitrate / acetonitrile; water / 12 h / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 12 h / 25 °C 2: dipotassium peroxodisulfate; silver nitrate / acetonitrile; water / 12 h / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: toluene-4-sulfonic acid With N-chlorobenzotriazole; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.25h; Stage #2: 4-bromo-aniline With triethylamine at 20℃; for 1.5h; | Typical Procedure for Conversion of Sulfonic Acids to Sulfonamides.N-benzyl-4-methylbenzenesulfonamide (Table 6, Entry 6) General procedure: To a cold solution of PPh3 (0.327 g, 1.25 mmol) in CH2Cl2 (3 mL), freshly preparedNCBT (0.188 g, 1.25 mmol) was added with continuous stirring. p-Toluenesulfonic acid(0.172 g, 1 mmol)was then added and stirringwas continued for 15min at room temperature.Benzylamine (0.267 g, 2.5 mmol) was added. The white suspension was neutralized by triethylamine (0.139 mL). Stirring was continued for 80 min at room temperature. Theprogress of the reaction was followed by TLC. Upon completion of the reaction, theconcentrated residue was passed through a short silica-gel column using n-hexane-ethylacetate (3:1) as eluent. N-Benzyl-4-methylbenzenesulfonamide was obtained with 90%(0.236 g) yield after removing the solvent under reduced pressure |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / Reflux; Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique 1.2: 16 h / 20 °C / Inert atmosphere; Schlenk technique 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 16 h / 0 °C / Inert atmosphere; Schlenk technique | ||
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0.17 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 12 h / Inert atmosphere |
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 16 h / 60 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / Reflux; Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 3: platinum(II) chloride / toluene / 12 h / Inert atmosphere; Molecular sieve; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With sodium iodide In water at 20℃; for 4h; Electrochemical reaction; | |
78% | With ethylene dibromide; sodium iodide In water at 60℃; for 8h; Schlenk technique; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With dipotassium peroxodisulfate; palladium diacetate; toluene-4-sulfonic acid In toluene at 20℃; for 24h; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 8 h / 80 °C 2: copper dichloride; triethylamine / toluene / 18 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: 4-nitrostyrene; N-(4-bromophenyl)-4-methylbenzenesulfonamide With bathophenanthroline; palladium diacetate; copper(II) acetate monohydrate; p-benzoquinone In toluene at 120℃; for 24h; Stage #2: With magnesium In methanol at 70℃; for 1h; Stage #3: phenylboronic acid With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In monoethylene glycol diethyl ether; water at 65℃; for 14h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Stage #1: 4-nitrostyrene; N-(4-bromophenyl)-4-methylbenzenesulfonamide With bathophenanthroline; palladium diacetate; copper(II) acetate monohydrate; p-benzoquinone In toluene at 120℃; for 24h; Stage #2: acrylic acid n-butyl ester With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In 1,2-dimethoxyethane; water at 125℃; for 15h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 4-nitrostyrene; N-(4-bromophenyl)-4-methylbenzenesulfonamide With bathophenanthroline; palladium diacetate; copper(II) acetate monohydrate; p-benzoquinone In toluene at 120℃; for 24h; Stage #2: 4-methyl-N-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In tetrahydrofuran; water at 70℃; for 0.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With bathophenanthroline; palladium diacetate; copper(II) acetate monohydrate; p-benzoquinone In toluene at 120℃; for 24h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 20℃; for 0.25h; | General procedure for the synthesis of N-arylsulfonamide General procedure: A 10 mL round bottom flask was charged with arylboronic acid (1 mmol), DBU (3 mmol), ethanol (2 mL) then CuI (10 mol%) and TsNBr2 (1.2 mmol) was added and stirred for 5-20 min at room temperature. After completion of the reaction as indicated by TLC, the reaction mixture was quenched by adding sodium thiosulphate (200mg approximately), and stirring was continued for nearly 20 min. The reaction mixture was then extracted with ethyl acetate (3x20 ml), dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography on silicagel (230-400) mesh with petroleum ether-ethyl acetate as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With ethanol; potassium <i>tert</i>-butylate; copper diacetate at 20℃; for 12h; | III. General experimental procedure for the reaction of chloramine T and arylboronic acid General procedure: A test tube with stir bar was charged with N-Chloro-N-sodiosulfonamide 2 (0.3 mmol), arylboronic acid 1 (0.36 mmol) and tBuOK (50.5 mg, 0.45 mmol). A solution of Cu(OAc)2 (2.7 mg,0.015 mmol) in EtOH (1.5 mL) was then added to the test tube. The reaction mixture was stirred under air at room temperature for 12 h, then the heterogeneous mixture was diluted with ethylacetate. The resulting mixture was directly filtered through a pad of silica gel, then the silica gelwas eluted with ethyl acetate. The organic solutions was combined, and the solvent was removedunder reduced pressure. The crude product was purified by silica-gel column chromatography toafford the desired product. |
61% | With copper(l) iodide; potassium carbonate In water at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nickel(II) bromide dimethoxyethane; Ir[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine]2(1,10-phenantroline)PF6; Bathocuproine; diisopropylamine; magnesium bromide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; Irradiation; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With iron In water at 60℃; for 36h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With lithium hydroxide In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate at 80℃; for 12h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 0.17 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 12 h / Inert atmosphere 3.1: tetrakis(actonitrile)copper(I) hexafluorophosphate / tetrahydrofuran / 18 h / 25 °C / Schlenk technique; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone at 60℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With nickel(II) bromide 2-methoxyethyl ether complex; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In tetrahydrofuran at 60℃; for 16h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With 5,5'-dimethyl-2,2'-bipyridine; nickel(II) bromide 2-methoxyethyl ether complex; zinc In tetrahydrofuran at 60℃; for 16h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | Stage #1: N-(4-bromophenyl)-4-methylbenzenesulfonamide With caesium carbonate In propan-1-ol at 20℃; for 0.0833333h; Inert atmosphere; Darkness; Stage #2: 1-ethynyl-1,2-benziodoxol-3(1H)-one In propan-1-ol at 20℃; for 0.5h; Inert atmosphere; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | Stage #1: N-(4-bromophenyl)-4-methylbenzenesulfonamide With pyridine; copper(II) chloride monohydrate; oxygen; sodium carbonate In toluene at 70℃; for 0.25h; Stage #2: 3,3-Dimethylbut-1-yne In toluene at 70℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: copper(II) chloride monohydrate; sodium carbonate; pyridine; oxygen / toluene / 0.25 h / 70 °C 1.2: 4 h / 70 °C 2.1: trifluorormethanesulfonic acid / dichloromethane / -40 °C / Molecular sieve; Inert atmosphere; Green chemistry |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: N-(4-bromophenyl)-4-methylbenzenesulfonamide With potassium carbonate In isopropyl alcohol at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-ethynyl-1,2-benziodoxol-3(1H)-one In isopropyl alcohol at 25℃; for 0.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With nickel(II) chloride hexahydrate; cadmium(II) sulphide; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl acetamide at 55℃; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: <i>p</i>-toluidine With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: With sodium tetrafluoroborate In water Stage #3: 4-bromonitrosobenzene With cyclohexa-1,4-diene; 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate In acetonitrile at 60℃; for 16h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 8 h / 65 °C 2: (2R,2'R)-2,2'-((2-iodo-1,3-phenylene)bis(oxy))bis(N-methyl-3-phenylpropanamide); pyridine hydrogenfluoride; triethylamine tris(hydrogen fluoride); Selectfluor / dichloromethane / 24 h / 20 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With NH4HCO3; 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; for 12h; Irradiation; | 7 Example 7 Under LED illumination conditions, at room temperature, under an empty atmosphere, in a dry reaction tube, sodium p-toluene sulfonate (0.2 mmol), 4-bromonitrobenzene (0.4 mmol), biboronic acid pinaster (B2pin2) (0.4 mmol), ammonium bicarbonate (NH4HCO3) (0.4 mmol) and solvent tetrahydrofuran ( THF) (1 mL), followed by a 12-hour reaction at room temperature, after which the column chromatography was separated to obtain the product, with a yield of 95%. |
72% | Stage #1: para-nitrophenyl bromide With tetrahydroxydiborane In methanol; water monomer at 100℃; for 8h; Schlenk technique; Stage #2: p-toluenesulfinic acid sodium salt With iodine In methanol; water monomer at 35℃; for 3h; Schlenk technique; | 2. General procedure for synthesis of N-arylsulfonamides General procedure: In a 20 mL schlenk tube, nitrobenzene 1 (0.25 mmol), B2(OH)4 (2 mmol, 180 mg), solvent MeOH: H2O (V:V=1:1) (2 mL) were added. The reaction mixture was stirred at 100 °C for 8 h. Then Ar2SO2Na 2 (0.5 mmol, 2 eq) and I2 (0.25 mmol, 1eq) were added, the mixture was stirred at 35 °C for 3 h under air. After the reaction was completed, the mixture was extracted with ethyl acetate (3 × 5 mL). The combined organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography to give the corresponding N-arylsulfonamides 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With copper(l) iodide; potassium carbonate; 1,3-diphenylpropanedione In ethanol at 25℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With nickel(II) bromide dimethoxyethane; 4,4'-Dimethoxy-2,2'-bipyridin; tetrabutylammomium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 20℃; for 6h; Inert atmosphere; Sealed tube; Electrochemical reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Stage #1: toluene-4-sulfonic acid hydrazide With N-chloro-succinimide In acetonitrile at 20℃; for 2h; Stage #2: 4-bromo-aniline With triethylamine at 20℃; for 2h; | 4.4. General Procedure for One-Port Reaction with Nucleophile General procedure: N-Chlorosuccinimide 2a (0.6 mmol, 2.0 equiv) was added to a solution of 4-methylbenzenesulfonhydrazide 1a (0.3 mmol) in CH3CN (2 mL) in one portion. Themixture was stirred at room temperature for 2 h. Then, Et3N (0.6 mmol, 2.0 equiv) andnucleophile (0.6 mmol, 2.0 equiv) were added to the above reaction system, and the mixturewas stirred at room temperature for 2 h. The solvent was removed, and the residuewas purified by flash column chromatography (PE/EA) to provide the correspondingsulfonamides and sulfonate 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With air In dichloromethane at 20℃; Electrochemical reaction; Electrolysis; Flow reactor; Green chemistry; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); formic acid / tetrahydrofuran; 1,2-dichloro-ethane / 12 h / 40 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: tris-(dibenzylideneacetone)dipalladium(0); formic acid; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tetrahydrofuran; 1,2-dichloro-ethane / 12 h / 40 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 16 h / 60 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere 3: silver(I) triflimide; (triphenylphosphine)gold(I) chloride / dichloromethane / 0.33 h / 25 °C / Inert atmosphere |
Tags: 32857-48-0 synthesis path| 32857-48-0 SDS| 32857-48-0 COA| 32857-48-0 purity| 32857-48-0 application| 32857-48-0 NMR| 32857-48-0 COA| 32857-48-0 structure
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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