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CAS No. : | 7454-54-8 | MDL No. : | MFCD00159375 |
Formula : | C12H10BrNO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZCUJCYISOKHAAW-UHFFFAOYSA-N |
M.W : | 312.18 | Pubchem ID : | 564228 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 chloroform; hypochloric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chlorosulphuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With pyridine In dichloromethane at 20℃; for 1h; Inert atmosphere; | |
95% | In ethanol; water at 25℃; for 0.166667h; | |
75% | With pyridine; dmap In dichloromethane for 12h; Inert atmosphere; |
57.3% | With pyridine In dichloromethane at 20℃; for 6h; Inert atmosphere; | 1 Step 1 : Synthesis of 4-bromo-N-phenylbenzenesulfonamide 4-Bromobenzenesulfonyl chloride (2.00 g, 7.82 mmol, 1.0 eq), aniline (0.87 g, 9.34 mmol, 1.2 eq) and pyridine (3.00 g, 39.06 mmol, 5.0 eq) were dissolved in dichloromethane (25 mL) under nitrogen atmosphere and the solution was stirred at ambient temperature for 6 h. After complete consumption of starting material, the reaction mixture was diluted with dichloromethane and washed with 0.5 N aq HC1 followed by water, saturated aq NaHC03 and brine. The organic extract was then dried over anhydrous sodium sulfate, filtered, and solvent evaporated from the filtrated under reduced pressure to afford 4-bromo-N-phenylbenzenesulfonamide as yellow solid (1.4 g, 57.3%). LCMS: Purity 99.69%. MS calculated for [M] 310.96 and found [M-H]+ 309.88. |
35% | With pyridine at 0 - 20℃; for 1h; Inert atmosphere; | |
With pyridine at 20℃; | ||
With pyridine for 0.0833333h; Heating; | ||
With pyridine In dichloromethane at 20℃; | ||
In pyridine for 0.5h; Heating; | ||
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 0.5h; | 40.a ) 4-Bromo-λ/-phenylbenzenesulfonamideAniline (1.837 g, 19.725 mmol) was added to a solution of 4- bromobenzenesulfonyl chloride (2.5 g, 9.784 mmol) and DIPEA (3 ml_, 17.524 mmol) in THF (50 ml_). The reaction mixture was allowed to react for 30 min and poured into H2O (120 ml_). It was taken up to pH = 1 with HCI (15% aqueous solution) and extracted with EtOAc (2x100 ml_). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated, to furnish the product as a yellow coloured oil. The crude residue was submitted to next step without purification. | |
With pyridine In dichloromethane for 5h; | Synthesis of N-Phenyl Benzenesulfonamide Derivatives General procedure: N-phenyl benzenesulfonamide, N-phenyl [2H5]benzenesulfonamide, N-phenyl mesitylenesulfonamide, N-phenyl p-toluenesulfonamide, N-phenyl p-nitrobenzenesulfonamide, and N-phenyl pbromobenzenesulfonamide were synthesized by adding aniline (20 mg) to solutions of benzenesulfonyl chloride, [2H5]benzenesulfonyl chloride, mesitylenesulfonyl chloride, ptoluenesulfonylchloride, p-nitrobenzenesulfonyl chloride, or p-bromobenzenesulfonyl chloride (40 mg), respectively, in dichloromethane (2 mL) and pyridine (0.1 mL). After 5 h, the mixture was neutralized with concentrated hydrochloric acid (1 mL) and the aqueous phase was removed. The organic phase was then evaporated to obtain the desired compound as a solid residue. | |
With triethylamine In dichloromethane at 20℃; Inert atmosphere; Schlenk technique; | ||
With triethylamine In dichloromethane at 22℃; | ||
With pyridine In dichloromethane | ||
With pyridine at 0℃; Inert atmosphere; | 2.1. General Method for Reaction 1 General procedure: (i) To a solution of an aromatic amine compound (1.38mmol) in pyridine (3 mL), an aromatic sulfonyl chloride(1.38 mmol) solution in pyridine (3 mL) was added dropwiseat 0 oC under N2. The mixture was stirred overnight. Pyridinewas removed under reduced pressure. The oily residue wasdissolved in ethyl acetate (20 mL), washed with water (2 x10 mL) and brine, and concentrated. The residue was subjectedto column chromatography (silica gel) to give a sulfonamideproduct in 66-89% yield. | |
In pyridine at 0 - 20℃; | Quinone Imine Ketals 1; General Procedure18 General procedure: To a stirred solution of the corresponding aniline (10 mmol, 1.0 equiv) in pyridine (20 mL) at 0 °C, the corresponding sulfonyl chloride (11 mmol, 1.1 equiv) was added slowly. The reaction mixture was allowed to warm to ambient temperature, and was stirred overnight and monitored by TLC. When the aniline was completely consumed, the pyridine was evaporated under reduced pressure. The residue was quenched with EtOAc (10 mL) and 1 N HCl (10 mL), then the mixture was extracted with EtOAc (3 × 20 mL) and saturated NaHCO3 (3 × 10 mL). The combined organic layers were washed with brine, dried with anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc, 10:1-4:1) to give the corresponding N-protected aniline. To a solution of the N-protected aniline (2 mmol, 1.0 equiv) in distilled MeOH (20 mL) was added phenyliodine diacetate (PIDA) (2.4 mmol, 1.2 equiv) under nitrogen atmosphere, and the mixture was stirred at room temperature and monitored by TLC. When the N-protected aniline was completely consumed, the reaction was quenched with saturated NaHCO3 (20 mL) and then the mixture was extracted with EtOAc (3 × 20 mL). The combined organic layers were washed with brine (20 mL) and dried with anhydrous Na2SO4, then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc, 15:1-6:1) to give the corresponding quinone imine ketal 1. | |
With 2,6-dimethylpyridine at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36.2% | at 140℃; for 0.666667h; Yield given. Title compound not separated from byproducts; | |
36.2% | at 140℃; for 0.666667h; | |
36.2% | at 140℃; for 0.666667h; Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Rk. m. Butyllithium; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With tert.-butylhydroperoxide; caesium carbonate; palladium(II) bromide In acetonitrile at 20℃; for 24h; | General procedure: In this experiment, the amount of S-arylsulfonamide added was 0.3 mmol, the amount of aryl hydrazine added was aryl hydrazine, the amount of palladium bromide added was 10 mol%, and the amount of cesium carbonate added was 0.6 mmol. The amount of acetonitrile added was 1.5 ml, and the amount of t-butanol peroxide added was 2.0 equiv. The reaction temperature was room temperature and the reaction time was 24 hours. The experimental conditions and experimental results of the third group of experiments are shown in Table 3. |
nach Shepherd, J. org. Chem. 12 <1947> 275; | ||
4-Brom-benzol-sulfonsaeure-(1)-anhydrid, Anilin; |
4-Brombenzolsulfonylchlorid, Anilin; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine; diethylazodicarboxylate In toluene at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: PPh3; DEAD / toluene / 0 - 20 °C 2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 70 percent / sodium hydride / dimethylformamide / 3 h / 0 - 20 °C 2: 46 percent / 2-methyl-propan-2-ol / 25 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 70 percent / sodium hydride / dimethylformamide / 3 h / 0 - 20 °C 2: 42 percent / 2-methyl-propan-2-ol / 18 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 70 percent / sodium hydride / dimethylformamide / 3 h / 0 - 20 °C 2: 62 percent / 2-methyl-propan-2-ol / 12 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SO3; H2SO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With bis-triphenylphosphine-palladium(II) chloride; triethylamine In DMF (N,N-dimethyl-formamide) at 120℃; for 72h; | 319.a 4-(2-Cyanovinyl)-N-phenylbenzenesulfonamide a) 4-(2-Cyano-vinyl)-N-phenyl-benzenesulfonamide A mixture of 2.88 g (0.009 mol) 4-bromo-N-phenyl-benzenesulfonamide, 0.59 g (0.011 mol) acrylonitrile, 4.65 ml (0.033 mol) triethylamine and 129 g (0.0002 mol) bis(triphenyl-phosphine)palladium(II)chloride in 50 ml dimethylformamide were stirred at 120° C. for 72 hours. The mixture was extracted with saturated aqueous sodiumbicarbonate solution and dried with sodiumsulfate. Chromatography on silicagel with hexane/ethylacetate 7/3 gave 1.73 g (69%) (E)/(Z)-4-(2-cyano-vinyl)-N-phenyl-benzenesulfonamide as a white solid. MS m/e (%):MS m/e (%): 283 (M-H-, 100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate In 1,4-dioxane at 90℃; for 6h; Heating; | 24 24. 4-F2-R2-(4-METHOXYPYRIDIN-2-YLLETHYLL-3H-IMIDAZOR4Q5-BIPYRIDIN-6-YL} N-PHENVL-BENZENESULFONAMIDE A mixture of 0.468 g of N-phenyl-4-bromo-benzenesulfonamide, 0.42 g of BIS- (PINACOLATO)-DIBORON, 0. 025 g of 1, 1 -BIS- (DIPHENYLPHOSPHINO)-FERROCENE, 0.033 g of [1, 1'-bis (diphenylphosphino)- ferrocene] palladium-dichloride (complex with CH2Cl2), OSA42 g of potassium acetate in 6 ml of degassed dioxane are heated to 90°C in a sealed tube under N2 for 6 hours. To the resulting mixture 5 ml of degassed dioxane, 0.371 g of 2- [2- (4-METHOXYPYRIDIN-2-YL) ETHYL]-6-IODO-3H-IMIDAZO [4,5- b] pyridine (starting material A1), 0.113 g OF TETRAKIS (TRIPHENYLPHOSPHINE)-PALLADIUM (O) and a solution of 0.27 g of potassium carbonate and 0.083 g of lithium chloride in 5 ml of degassed water are added under N2. The tube is sealed again, the mixture is heated to 120° UNDER N2 for 16 hours and, after cooling, addition of water and adjusting the pH to 7, it is extracted three times with dichloromethane. The combined organic phases are dried over sodium sulfate, concentrated and the residue is chromatographed on a silica gel column (DICHLOROMETHANE/METHANOL 28-15: 1). Concentration of the chromatographically pure fractions and crystallisation from acetonitril gives 0.125 g of the title compound as a solid of m. p. 231-233°C. The mass spectrum shows the molecular peak MH+ at 507.3 Da. | |
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 20℃; Inert atmosphere; | ||
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 20℃; Inert atmosphere; |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 85℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 2h; | 40.b b) tert-Butyl (4-bromophenyl)sulfonyl(phenyl)carbamateBoC2O (2.80 g, 12.829 mmol) was added to a solution of 4-bromo-/V- phenylbenzenesulfonamide (9.784 mmol), DMAP (150 mg, 1.227 mmol) and DIPEA (5.0 ml_, 29.207 mmol) in CH3CN (80 ml_). The reaction mixture was stirred at r.t. for 2 h, poured into H2O (200 ml_) and extracted with EtOAc (200 ml_). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (5→10% EtOAc/hexanes), to afford 3.86 g of tert-butyl (4- bromophenyl)sulfonyl(phenyl)carbamate (white solid, yield: 79%). El MS: m/z = 413 (M+1 ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: (R)-4-(2-(2-methylpyrrolidin-1-yl)ethyl)phenylboronic Acid; 4-bromo-N-phenylbenzenesulfonamide With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; benzene at 100℃; for 1h; Microwave irradiation; Stage #2: With hydrogenchloride In diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-bromo-N-phenylbenzenesulfonamide With potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 160℃; for 0.666667h; Microwave irradiation; Stage #2: 6-bromo-2-[2-(4-methoxy-pyridin-2-yl)-vinyl]-oxazolo[4,5-b]pyridine With sodium carbonate In 1,4-dioxane; water at 140℃; for 0.333333h; Microwave irradiation; | A9 Example A9; 2-[2-(4-Methoxy-pyridin-2-yl)-vinyl]-6-[4-(N-phenylamino-1-sulfonyl)-phenyl]-oxazolo[4,5- b]pyridine; A stirred mixture of 0.16 g (0.50 mmol) 4-bromo-N-phenyl-benzenesulfonamide, 0.14 g (0.55 mmol) bis(pinacolato)-diboron, 8.3 mg (0.015 mmol) 1 ,1'-bis(diphenylphosphino)ferrocene (dppf), 11 mg(0.015 mmol) PdCI2(dppf)xCH2CI2 and 0.15 g (1.50 mmol) potassium acetate in 3 ml absolute dioxane is heated to 16O0C for 40 min with a microwave equipment. After cooling to room temperature 0.11 g (0.33 mmol) 6-bromo-2-[2-(4-methoxy-pyridin-2-yl)-vinyl]-oxazolo[4,5-b]pyridine, 15.0 mg (0.02 mmol) PdCI2(PcHeX)3 and 1 ml of a 2 N aqueous Na2CO3 solution are added to the reaction mixture. The suspension is heated again with a microwave equipment to 14O0C for 20 min. For workup, the mixture is poured into 100 ml water and then extracted three times with CH2CI2. The combined organic phases are dried over MgSO4, filtered and concentrated in vacuo. Subsequent purification by silica gel chromatography [CH2CI2/CH3OH (98/2 parts by volume)] affords the title compound (0.17 g) as yellow crystals. The mass spectrum shows the molecular peak MH+ at 485.2 Da. EPO |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 130℃; for 20h; Inert atmosphere; Schlenk technique; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 130℃; for 20h; Inert atmosphere; Schlenk technique; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With 1,10-Phenanthroline; palladium(II) trifluoroacetate; oxygen In toluene at 140℃; for 40h; | 2 2.2. General procedure: 4-methyl-N-phenylbenzenesulfonamide (3a) General procedure: 2.2 General procedure: 4-methyl-N-phenylbenzenesulfonamide (3a) A 25 mL oven-dried reaction vessel was charged with Pd(TFA)2 (2.3 mg, 0.01 mmol), 1,10-phenanthroline (3.6 mg, 0.02 mmol), p-toluene sulfonamide (1a, 34.2 mg, 0.2 mmol), cyclohexanone (2a, 32 μL, 0.3 mmol). The reaction vessel was flushed with oxygen three times and then sealed. Toluene (0.7 mL) was added by syringe and the resulting solution was stirred at 140 °C for 40 h. After cooling to room temperature, the volatiles were removed under vacuum and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 4:1) to give the corresponding product 3a (39.9 mg) as white solid in 81% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: johnphos; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate / toluene / 80 - 100 °C / Inert atmosphere 2.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 20 °C 3.1: pyridine / dichloromethane / 0.08 h / 20 °C 3.2: 20 °C 4.1: trifluoroacetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: johnphos; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate / toluene / 80 - 100 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: johnphos; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate / toluene / 80 - 100 °C / Inert atmosphere 2.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 20 °C 3.1: pyridine / dichloromethane / 0.08 h / 20 °C 3.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In toluene at 80 - 100℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(ll) sulfate pentahydrate; potassium carbonate; 1,7-phenanthroline In toluene at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-bromo-N-phenylbenzenesulfonamide 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; |
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: potassium acetate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 20 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; acetonitrile / 0.17 h / 150 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 20 °C / Inert atmosphere 2: sodium carbonate / water; acetonitrile / 0.17 h / 150 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium acetate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 20 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; acetonitrile / 0.17 h / 150 °C / Inert atmosphere 3: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; acetonitrile / 0.17 h / 150 °C / Inert atmosphere; Microwave irradiation | ||
Multi-step reaction with 3 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 20 °C / Inert atmosphere 2: sodium carbonate / water; acetonitrile / 0.17 h / 150 °C / Inert atmosphere 3: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; acetonitrile / 0.17 h / 150 °C / Inert atmosphere; Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium acetate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 20 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; acetonitrile / 0.17 h / 150 °C / Inert atmosphere; Microwave irradiation | ||
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 20 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; acetonitrile / 0.17 h / 150 °C / Inert atmosphere; Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; trifluoroacetic acid In toluene at 0℃; for 1h; | One-pot procedure for the preparation of mono N-arylsulfonamide (Table 4) General procedure: Upon completion of General procedure I, as determined by TLC, the reaction mixture (1.00 mmol scale) was cooled to 0 °C. Cold trifluoroacetic acid/water (9:1 mL) was slowly added. The reaction was stirred 1 h at 0 °C at which time the reaction was diluted with toluene. All volatiles were removed with a rotary evaporator, and the product isolated by silica gel chromatography using the solvent system indicated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; sodium hydrogen sulfite; iron(II) chloride In dimethyl sulfoxide at 60℃; for 12h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,10-Phenanthroline; potassium carbonate; copper(II) sulfate In toluene at 70℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; copper(II) sulfate; 1,10-Phenanthroline / toluene / 12 h / 70 °C 2: IPrAuNTf<SUB>2</SUB> / dichloromethane / 0.17 h / 20 °C / Schlenk technique; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; iron(III) chloride hexahydrate; N,N`-dimethylethylenediamine / toluene / 12 h / 100 °C 2: 2-bromopyridine-N-oxide; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate / water / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 11h; Inert atmosphere; | |
With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 100℃; for 12h; | ||
With 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium carbonate In toluene at 80℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N,N`-dimethylethylenediamine; potassium carbonate; iron(III) chloride hexahydrate / toluene / 12 h / 90 °C 2: 8-ethylquinoline N-oxide; zinc trifluoromethanesulfonate / 1 h / 20 - 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With pyridine; palladium(II) hydroxide In N,N-dimethyl-formamide at 90℃; for 20h; Inert atmosphere; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; iron(III) chloride hexahydrate; N,N`-dimethylethylenediamine / toluene / 11 h / 90 °C / Inert atmosphere 2: [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate / 1,2-dichloro-ethane / 5 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.7 g | With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere; Schlenk technique 2: water; fac-Ir(ppy)<SUB>3</SUB> / N,N-dimethyl-formamide / 12 h / 20 °C / Schlenk technique; Irradiation; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; copper(l) iodide; <i>L</i>-proline / dimethyl sulfoxide / 18 h / 90 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 3: hydrogenchloride / dichloromethane; 1,4-dioxane; water / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; copper(l) iodide; <i>L</i>-proline / dimethyl sulfoxide / 18 h / 90 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18.7% | With copper(l) iodide; potassium carbonate; <i>L</i>-proline In dimethyl sulfoxide at 90℃; for 18h; | 2 Step 2: Synthesis of tert-butyl 4-(4-(N-phenylsulfamoyl)phenyl)piperazine-l-carboxylate A mixture of 4-bromo-N-phenylbenzenesulfonamide (1.00 g, 3.20 mmol, 1.0 eq), tert-butyl piperazine-l-carboxylate (0.71 g, 3.81 mmol, 1.2 eq), K2C03 (0.89 g, 6.40 mmol, 2.0 eq), Cul (0.12 g, 0.640 mmol, 0.2 eq) and L-proline (0.11 g, 0.955 mmol, 0.3 eq) in DMSO (15 mL) was stirred at 90° C for 18 h. After complete consumption of starting material, the mixture was cooled to ambient temperature and partitioned between water and ethyl acetate. The organic extract was separated and the aqueous extract was again extracted with ethyl acetate. The combined organic extract was washed with brine, dried over anhydrous Na2S04, filtered and solvents evaporated from the filtrate under reduced pressure to obtain a crude, which was purified by flash chromatography on silica gel, 230-400 mesh, using gradient of ethyl acetate in hexanes as eluent to obtain tert-butyl 4-(4-(N-phenylsulfamoyl)phenyl)piperazine-l-carboxylate as yellow solid, yield (0.25 g, 18.7%). LCMS: Purity 84.26%. MS calculated for [M] 417.17 and found [M-H]+ 416.08. Step 3: Synthesis of N-phenyl-4-(piperazin-l-yl)benzenesulfonamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In acetone Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / Reflux 2: palladium dichloride; copper(I) bromide; lithium carbonate / 1,4-dioxane / 20 h / 140 °C / Schlenk technique; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With dichloro bis(acetonitrile) palladium(II); silver(I) acetate In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; Schlenk technique; | General procedure for the synthesis of 3 General procedure: Under the argon atmosphere, a Schlenk tube (15 mL) equipped with a magnetic bar was loaded with the sulfonamide 1 (0.5 mmol), sodium arylsulfinates 2 (0.6 mmol, 1.2 equiv.), Pd(MeCN)2Cl2 (6.5 mg, 5 mol%) and AgOAc (166.9 mg, 1.0 mmol) in one portion. Then, the mixture of 1,4-dioxane/DMSO (3.5 mL in a 9:1 ratio) was added to obtain a clear solution and the reaction mixture was allowed to stir at 120 °C for 24 h. After cooling to room temperature, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated and the oily crude product was purified by column chromatography using silica gel (200-300 mesh) as stationary phase and a petroleum ether and ethyl acetate (3/1) as eluent to give the N-aryl sulfonamides 3 in noted yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With iron In water for 0.833333h; | 15 Preparation of 4-bromo-N-phenylbenzenesulfonamide In a 25 mL round bottom flask, 1.23 g of nitrobenzene, 3.83 g of 4-bromobenzenesulfonyl chloride, 1.96 g of iron powder, 10 mL of water were added in sequence, and the mixture was stirred at 35 W/40 KHz for ultrasonic stirring (600 rpm). The reaction was carried out for 50 minutes.The reaction was extracted with ethyl acetate.Recrystallization gave the corresponding N-(4-bromophenyl)benzenesulfonamide 2.90 g, yield 93%. |
66% | With iron In water at 60℃; for 36h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide 2: dipotassium peroxodisulfate / dimethyl sulfoxide / 24 h / 50 °C / Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: [bis(acetoxy)iodo]benzene / 20 °C / Inert atmosphere 2: 1,4-diaza-bicyclo[2.2.2]octane / ethanol / 2 h / 40 °C / Green chemistry |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [bis(acetoxy)iodo]benzene at 20℃; Inert atmosphere; | Quinone Imine Ketals 1; General Procedure18 General procedure: To a stirred solution of the corresponding aniline (10 mmol, 1.0 equiv) in pyridine (20 mL) at 0 °C, the corresponding sulfonyl chloride (11 mmol, 1.1 equiv) was added slowly. The reaction mixture was allowed to warm to ambient temperature, and was stirred overnight and monitored by TLC. When the aniline was completely consumed, the pyridine was evaporated under reduced pressure. The residue was quenched with EtOAc (10 mL) and 1 N HCl (10 mL), then the mixture was extracted with EtOAc (3 × 20 mL) and saturated NaHCO3 (3 × 10 mL). The combined organic layers were washed with brine, dried with anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc, 10:1-4:1) to give the corresponding N-protected aniline. To a solution of the N-protected aniline (2 mmol, 1.0 equiv) in distilled MeOH (20 mL) was added phenyliodine diacetate (PIDA) (2.4 mmol, 1.2 equiv) under nitrogen atmosphere, and the mixture was stirred at room temperature and monitored by TLC. When the N-protected aniline was completely consumed, the reaction was quenched with saturated NaHCO3 (20 mL) and then the mixture was extracted with EtOAc (3 × 20 mL). The combined organic layers were washed with brine (20 mL) and dried with anhydrous Na2SO4, then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc, 15:1-6:1) to give the corresponding quinone imine ketal 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; triethylamine In tetrahydrofuran at 24℃; for 24h; Irradiation; Inert atmosphere; Sealed tube; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; triethylamine In tetrahydrofuran at 24℃; for 24h; Irradiation; Inert atmosphere; Sealed tube; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tert.-butylhydroperoxide; copper acetylacetonate; caesium carbonate In water; acetonitrile at 100℃; for 12h; Schlenk technique; | 5. General procedure towards N-aryl sulfonamides 5 General procedure: Under the air atmosphere, a Schlenk tube (35 mL) equipped with a magnetic bar was loaded with the sulfonamide 4 (0.5 mmol), Cu(acac)2 (20 mol%), TBHP (70% in water, 2.0 equiv.), Cs2CO3 (2.0equiv.) in dry solvent MeCN (4.0 mL). Then the reaction mixture was allowed to stir at 60C for 12 h. After the completion of the reaction, as monitored by TLC analysis, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL x 3). The filtrate was concentrated, and the oily crude product was puried by column chromatography using silica gel (200-300 mesh) as stationary phase and a mixture of n-hexane and ethyl acetate (2:1) as eluent to give the corresponding arylated products 5 (Rf = ca.0.3 otherwise noted). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With sodium metabisulfite; copper(l) chloride In melt at 80℃; for 24h; Green chemistry; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 1,10-Phenanthroline; tetrakis(actonitrile)copper(I) hexafluorophosphate; potassium pyrosulfite; isopropyl alcohol at 70℃; for 48h; Sealed tube; Inert atmosphere; | |
65% | With potassium pyrosulfite; tetrabutyl-ammonium chloride; potassium carbonate In acetonitrile at 130℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In pyridine at 50℃; for 2h; | 1.1; 2.1; 3.1; 4.1; 5.1 (1) Synthesis of p-bromobenzenesulfonanilide Take a 100ml single-necked bottle, add 4.74g (0.02mol) of p-bromobenzenesulfonic acid, and add 100mL of pyridine, stir to dissolve, then add 2.23g (0.024mol) of aniline,Then slowly add the condensing agent EDC-HCl 5.73g (0.04mol) to the reaction solution in batches, then heat to 50 ° C to react for 2h,The pyridine was removed by rotary evaporation, the remaining water was poured into a separatory funnel, and an appropriate amount of ethyl acetate was added thereto for extraction 3 times, and the ethyl acetate layer was washed once with dilute hydrochloric acid water.The organic layers were combined, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 5.99 g of a white solid in 96% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 110℃; for 10h; Inert atmosphere; | 1.2; 2.2; 3.2; 4.2; 5.2 (2) Synthesis of benzenesulfonylaniline substituted with para-cyclopropane Weigh 3.12g (0.01mol) of p-bromobenzenesulfonanilide, add 15mL of dioxane and 5mL of water, stir and dissolve, and then weigh 0.86g (0.01mol) of cyclopropylboronic acid,Sodium carbonate 2.12g (0.05mol), Pd (dppf) Cl 21.16g (0.001mol), added to the reaction system, and then replaced with nitrogen 3 times, set the reaction temperature 110 reaction for 10h.After the reaction is completed, the solvent is distilled off under reduced pressure, and the residue is extracted with appropriate amount of water and ethyl acetate 3 times.After the extract was dried over anhydrous sodium sulfate, the solvent was removed by a rotary evaporator, and the resulting residue was purified by column to obtain 2.6 g of white body in 95% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide In N,N-dimethyl acetamide at 20℃; for 24h; Irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide In N,N-dimethyl acetamide at 20℃; for 24h; Irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide In N,N-dimethyl acetamide at 20℃; for 24h; Irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide In N,N-dimethyl acetamide at 20℃; for 24h; Irradiation; Inert atmosphere; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide In N,N-dimethyl acetamide at 20℃; for 24h; Irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With trimethylamine In ethanol for 1.16667h; Reflux; Green chemistry; | 2.5. N -Arylation of primary sulfonamides using Fe 3 O 4 -CSMet-Cu(II) catalyst General procedure: A 50 mL flask was filled with 0.5 mmol of primary sulfonamide, 0.5 mmol of arylboronic acid, 0.7 mmol of trimethylamine (Et 3 N), 0.02 g of Fe 3 O 4 -CSMet-Cu(II), and 7 mL of ethanol and the mix- ture thus obtained was stirred at reflux for the appropriate time (monitored using TLC). When the reaction was over, the reaction mixture was cooled and the catalyst was collected using an exter- nal magnet. After evaporation of ethanol, the solid residue was pu- rified by recrystallization from ethyl acetate and n-hexane to yield the appropriate product. The melting points of products matched those reported in our previous work and literature values [ 13 , 57 ]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium isocyanate / water / 0.33 h / Sonication; Green chemistry 2: trimethylamine / ethanol / 1.17 h / Reflux; Green chemistry |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; sodium hydrogencarbonate In N,N-dimethyl acetamide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; sodium hydrogencarbonate In N,N-dimethyl acetamide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; sodium hydrogencarbonate In N,N-dimethyl acetamide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 85 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 1 h / 120 °C / Microwave irradiation; Inert atmosphere; Alkaline conditions |
Tags: 7454-54-8 synthesis path| 7454-54-8 SDS| 7454-54-8 COA| 7454-54-8 purity| 7454-54-8 application| 7454-54-8 NMR| 7454-54-8 COA| 7454-54-8 structure
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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 |
Sorry,this product has been discontinued.
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