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[ CAS No. 138-38-5 ] {[proInfo.proName]}

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Chemical Structure| 138-38-5
Chemical Structure| 138-38-5
Structure of 138-38-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 138-38-5 ]

CAS No. :138-38-5 MDL No. :MFCD01365828
Formula : C8H11NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :MLTGAVXHWSDGIS-UHFFFAOYSA-N
M.W : 185.24 Pubchem ID :222870
Synonyms :

Calculated chemistry of [ 138-38-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.21
TPSA : 68.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.4
Log Po/w (XLOGP3) : 1.31
Log Po/w (WLOGP) : 1.98
Log Po/w (MLOGP) : 0.97
Log Po/w (SILICOS-IT) : 0.73
Consensus Log Po/w : 1.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.05
Solubility : 1.64 mg/ml ; 0.00888 mol/l
Class : Soluble
Log S (Ali) : -2.35
Solubility : 0.828 mg/ml ; 0.00447 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.76
Solubility : 0.325 mg/ml ; 0.00175 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.63

Safety of [ 138-38-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 138-38-5 ]

* 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.

  • Downstream synthetic route of [ 138-38-5 ]

[ 138-38-5 ] Synthesis Path-Downstream   1~65

  • 1
  • [ 90-46-0 ]
  • [ 138-38-5 ]
  • 4-ethyl-benzenesulfonic acid xanthen-9-ylamide [ No CAS ]
  • 2
  • [ 100-41-4 ]
  • [ 66294-51-7 ]
  • [ 138-38-5 ]
  • 3
  • [ 16712-69-9 ]
  • [ 138-38-5 ]
YieldReaction ConditionsOperation in experiment
450 kg With ammonium hydroxide; for 2h;Large scale; 300 kg of ethylbenzene was added to the 2000L reactor.15 kg of sodium chloride and 2000 kg of chloroform, temperature control -5 C,990 kg of chlorosulfonic acid was added dropwise; after the addition was completed, the reaction was maintained at -5 C for 1 hour.Heating to 15 C for 2 hours; temperature control below 20 C,Slowly add 200 kg of water to extract the reaction; stir for half an hour.The lower layer of sulfuric acid was removed by static stratification. Within 5 hours,The upper organic phase was added dropwise to 700 kg of 20% aqueous ammonia and stirring was continued for 2 hours.Centrifugation gave an off-white solid.Transfer the centrifuged crude to a 2000L reactor.Add 300 kg of methanol and 600 kg of water.The temperature is raised to 80 C by heating, the solid is completely dissolved, and the heat is discharged to the crystallizer.Stir and cool to 10-15 C for 4 hours.The crystals were obtained by centrifugation and dried under vacuum to obtain 450 kg of product, the yield was 86%.The purity is 99.8%.
  • 5
  • [ 138-38-5 ]
  • [ 3173-53-3 ]
  • [ 965-82-2 ]
  • 6
  • [ 138-38-5 ]
  • [ 107-13-1 ]
  • [ 100720-12-5 ]
  • 7
  • [ 17988-51-1 ]
  • [ 138-38-5 ]
  • 8
  • [ 138-38-5 ]
  • [ 104-12-1 ]
  • [ 102607-92-1 ]
  • 10
  • [ 138-38-5 ]
  • [ 122-51-0 ]
  • [ 100981-70-2 ]
  • 11
  • [ 696-59-3 ]
  • [ 138-38-5 ]
  • [ 891392-78-2 ]
  • 12
  • [ 138-38-5 ]
  • (1R,2R,4S,5S,6R)-6-Bromomethyl-3-oxa-tricyclo[3.2.1.02,4]octane [ No CAS ]
  • (1R,2S,3S,6S,7R)-4-(4-Ethyl-benzenesulfonyl)-4-aza-tricyclo[4.2.1.03,7]nonan-2-ol [ No CAS ]
  • 14
  • 1-ethyl-benzene-sulfonyl fluoride-(4) [ No CAS ]
  • [ 138-38-5 ]
  • 16
  • [ 138-38-5 ]
  • [ 762-42-5 ]
  • [ 603-35-0 ]
  • (Z)-dimethyl 2-(4-ethylbenzenesulfonylamino)-3-(triphenylphosphanylidene)-succinate [ No CAS ]
  • (E)-dimethyl 2-(4-ethylbenzenesulfonylamino)-3-(triphenylphosphanylidene)-succinate [ No CAS ]
  • 17
  • C8H9ClNO2S(1-)*Na(1+) [ No CAS ]
  • [ 138-38-5 ]
  • 18
  • [ 138-38-5 ]
  • [ 3168-01-2 ]
  • 19
  • [ 138-38-5 ]
  • [ 113412-15-0 ]
  • 20
  • [ 138-38-5 ]
  • [ 220948-20-9 ]
  • 21
  • [ 138-38-5 ]
  • [ 220948-21-0 ]
  • 22
  • [ 138-38-5 ]
  • [ 220948-17-4 ]
  • 23
  • [ 138-38-5 ]
  • [ 220948-22-1 ]
  • 24
  • [ 138-38-5 ]
  • [ 220948-19-6 ]
  • 25
  • [ 138-38-5 ]
  • (S)-(-)-4-(1-hydroxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide [ No CAS ]
  • 26
  • [ 138-38-5 ]
  • (R)-(+)-4-(1-hydroxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide [ No CAS ]
  • 27
  • [ 138-38-5 ]
  • [ 220948-18-5 ]
  • 28
  • [ 138-38-5 ]
  • [ 220948-23-2 ]
  • 29
  • [ 138-38-5 ]
  • [ 220948-24-3 ]
  • 30
  • [ 138-38-5 ]
  • [ 220948-26-5 ]
  • 31
  • [ 138-38-5 ]
  • [ 220948-27-6 ]
  • 32
  • [ 138-38-5 ]
  • (2,4-Dichloro-phenyl)-[1-(4-ethyl-benzenesulfonyl)-1H-pyrrol-3-yl]-methanone [ No CAS ]
  • 33
  • [ 138-38-5 ]
  • (2,4-Dichloro-phenyl)-[1-(4-ethyl-benzenesulfonyl)-1H-pyrrol-3-yl]-methanol [ No CAS ]
  • 34
  • [ 138-38-5 ]
  • [ 100981-64-4 ]
  • 35
  • [ 128254-32-0 ]
  • [ 138-38-5 ]
  • 36
  • [ 219762-39-7 ]
  • [ 138-38-5 ]
  • 3-(2-chloro-4-phenylbenzyl)-5-[(4-ethylbenzene)sulfonylcarbamoyl]-2-methyl-3H-imidazo[4,5-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In the same manner as in Example 1, 3-(2-chloro-4-phenylbenzyl)-5-[(4-ethylbenzene)sulfonylcarbamoyl]-2-methyl-3H-imidazo[4,5-b]pyridine (213 mg) was obtained as colorless crystals from 3-(2-chloro-4-phenylbenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (200 mg) and <strong>[138-38-5](4-ethylbenzene)sulfonamide</strong> (147 mg). 1H-NMR(CDCl3): 1.22(3H, t, J=8 Hz), 2.63-2.75(5H, m), 5.62(2H, s), 6.88(1H, d, J=8 Hz), 7.29(2H, d, J=8 Hz), 7.36-7.50(4H, m), 7.60(2H, d, J=8 Hz), 7.73(1H, d, J=2 Hz), 8.01(2H, d, J=8 Hz), 8.07(1H, d, J=8 Hz), 8.11(1H, d, J=8 Hz). Mass(ESI): m/z 529 (M-1) mp: 205-206 C.
  • 37
  • [ 206066-38-8 ]
  • [ 138-38-5 ]
  • [ 438003-26-0 ]
YieldReaction ConditionsOperation in experiment
With diaza-bicyclo-undecene; 1,1'-carbonyldiimidazole; EXAMPLE 119 Production of 3-(2,4-dichlorobenzyl)-5-((4-ethylbenzene)sulfonylcarbamoyl)-2-methylindole (149) According to the method of Example 106, obtained is 3-(2,4-dichlorobenzyl)-5-((4-ethylbenzene)sulfonylcarbamoyl)-2-methylindole (149) (0.108 g) from 5-carboxy-3-(2,4-dichlorobenzyl)-2-methylindole (0.334 g), N,N'-carbonyldiimidazole (0.243 g), <strong>[138-38-5](4-ethylbenzene)sulfonamide</strong> (0.278 g) and diazabicycloundecene (0.228 g). 1H-NMR (DMSO-d6, delta ppm): 1.18 (3H, t, J=7.5 Hz), 2.28 (3H, s), 2.67 (2H, q, J=7.3 Hz), 4.07 (2H, s), 6.91 (1H, d, J=8.3 Hz), 7.25 (1H, d, J=7.5 Hz), 7.31 (1H, d, J=8.4 Hz), 7.44 (2H, d, J=7.9 Hz), 7.54 (1H, d, J=8.6 Hz), 7.60 (1H, s), 7.87 (2H, d, J=8.0 Hz), 7.97 (1H, s), 11.37 (1H, s), 12.10 (1H, brs). IR (Nujol): 1682 cm-1.
  • 38
  • [ 1336-21-6 ]
  • [ 16712-69-9 ]
  • [ 138-38-5 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; trichlorophosphate; In ethylbenzene; water; A. A mixture of 53.08 g (0.5 m) of ethylbenzene and 46.0 ml (0.5 m) of phosphorus oxychloride was heated to approximately 50 C. and 51.5 g (0.525 m) of 100 percent sulfuric acid was added slowly keeping the temperature in the range of 60 to 66 C. by adjusting the rate of addition. The reaction mixture was maintained at approximately 60 C. for approximately twenty-two and one-half hours and then maintained at about 90 C. for approximately five hours. After cooling, the reaction mixture was poured onto a slurry of 600.0 g of ice and 200.0 ml of water. After approximately forty-five minutes of stirring, the agitation was stopped and the layers separated. The lower layer containing the 4-ethylbenzenesulfonyl chloride was separated and washed with about 500 ml of cold water and separated. The upper water layer and the water wash were discarded. The oil organic liquid layer of 4-ethylbenzenesulfonyl chloride was added slowly to a slurry of 200.0 g of ice and 200.0 ml of concentrated ammonium hydroxide. The resulting mixture was stirred approximately thirty minutes at about 40 C. and then stirred overnight at ambient temperature. The solid was collected by filtration, washed with cold water and dried to obtain 81.71 g of 4-ethylbenzenesulfonamide, a white solid which melted at 107-109 C.
  • 40
  • [ 138-38-5 ]
  • [ 4349-62-6 ]
  • 4-ethyl-N-(2-hydroxybenzoyl)benzenesulfonamide [ No CAS ]
  • 41
  • [ 138-38-5 ]
  • [ 4349-62-6 ]
  • C22H21NO4S [ No CAS ]
  • 42
  • [ 138-38-5 ]
  • [ 189999-35-7 ]
  • [ 1469876-05-8 ]
YieldReaction ConditionsOperation in experiment
100% With copper diacetate; sodium carbonate; In ethylene glycol; isopropyl alcohol; at 90℃; for 16h;Inert atmosphere; General procedure: To a stirred solution of cyclicdiphenyliodonium trifluoromethanesulfonate (100 mg, 234 mmol, 1 eq) in iPrOH (1.8 mL) and ethylene glycol (0.2 mL), was added amine (4 eq), sodium carbonate (3 eq), Cu(OAc)2 (0.2 eq). The reaction proceeded at a reflux for 16 h under argon atmosphere before iPrOH was removed by a rotary evaporation. The remained mixture was partitioned between water and EtOAc, and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with H2O and brine, dried over anhydrous Na2SO4, evaporated in a vacuo. The residue was purified by column chromatography on a silica gel (PE/EtOAc) to provide carbazole derivatives. 5.1.2.20 9-((4-ethylphenyl)sulfonyl)-9H-carbazole (18) A white solid. HPLC tR = 6.063 min, 100%. 1H NMR (400 MHz, CDCl3) delta 8.34 (d, J = 8.4 Hz, 2H), 7.91 (d, J = 7.7 Hz, 2H), 7.74 (d, J = 6.6 Hz, 2H), 7.50 (t, J = 7.8 Hz, 2H), 7.36 (t, J = 7.5 Hz, 2H), 7.13 (d, J = 7.0 Hz, 2H), 2.57 (q, J = 7.3 Hz, 2H), 1.13 (td, J = 7.6, 2.2 Hz, 3H) ppm. 13C NMR (100 MHz, CDCl3) delta 150.8, 138.4, 135.3, 128.5, 127.4, 126.6, 126.4, 123.9, 120.0, 115.1, 28.7, 14.7 ppm. IR upsilon 2933, 1919, 1726, 1595, 1439, 1358, 1168, 970, 827, 751, 653, 578 cm-1. M.P. 122.1-123.0 C. LRMS (ESI, m/z): 336.2 [M + H]+. HRMS calcd for C20H16NO2S [M - H]-: 334.0902, found: 334.0906.
  • 43
  • [ 138-38-5 ]
  • [ 108-94-1 ]
  • [ 64329-90-4 ]
YieldReaction ConditionsOperation in experiment
79% With 1,10-Phenanthroline; palladium(II) trifluoroacetate; oxygen; In toluene; at 140℃; for 40h; 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 muL, 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.
  • 44
  • [ 138-38-5 ]
  • [ 121-44-8 ]
  • (E)-N,N-diethyl-N'-((4-ethylphenyl)sulfonyl)formimidamide [ No CAS ]
  • 45
  • [ 138-38-5 ]
  • [ 67-68-5 ]
  • [ 118-41-2 ]
  • 4,5,6-trimethoxy-2-(4-ethylphenylsulfonyl)isoindoline-1-one [ No CAS ]
  • 46
  • [ 138-38-5 ]
  • (3R,4S)-1-(4-methylphenyl)-3-(3-p-toluenesulfonate-n-propyl)-4-(4-nitrophenyl)-2-azetidinone [ No CAS ]
  • (3R,4S)-1-(4-methylphenyl)-3-[3-(4-ethylbenzenesulfonamido)propyl]-4-(4-nitrophenyl)-2-azetidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate; In acetonitrile; at 90℃; for 12h; General procedure: To a solution of (3R,4S)-2-azetidinone 4 (7.5 mmol) in THF (30 mL), 1 M aqueous solution of LiOH (40 mL)was added and the mixture stirred at room temperature. After 2 h, 1 M HCl wasadded to the reaction until pH was adjusted to 6. Then, the mixture wastransferred to a separatory funnel, extracted with ethyl acetate, dried overanhydrous Na2SO4, and concentrated to afford acid 5 of sufficient purity to be usedwithout further purification. 2 M THF solution of BH3·Me2S(7.32 mL) was added to compound 5(6.1 mmol) in 30 mL anhydrous THF at-10 C. The reaction was stirred for 8 h at roomtemperature and quenched by 1 M HCl (10 mL). Solvent was evaporated todryness, water (50 mL) added and the resulting mixture extracted with ethylacetate (3 × 30 mL). Collected organic layers were dried over anhydrous Na2SO4and solvent evaporated to dryness. 6was obtained by a silica gel column chromatography. To a solution of 6 (15.8 mmol), TsCl (3.6 g, 18.89 mmol)and catalytic amount of DMAP in CH2Cl2 (100 mL), Et3N(3.19 g, 31.52 mmol) was added in ice bath. The reaction proceeded overnightand was washed with water and brine. The organic layer was dried overanhydrous Na2SO4 and evaporated. The residue was purifiedby a silica gel column chromatography to give 7. For the synthesis of 8a-f,K2CO3 (0.19 g, 1.38 mmol) and substituted aromaticsulfonamide (1.38 mmol) were added to the solution of 7 (0.69 mmol) in CH3CN (5 mL). The mixture was stirredat 90 C for 12 h until complete by TLC. Solvent was concentrated, water (12mL) added and the resulting mixture extracted with CH2Cl2.Collected organic layers were washed with 3 M aqueous solution of NaOH (3 ×4 mL) and water (3 × 4.8 mL), dried over anhydrous Na2SO4 andevaporated. Initially target compounds 8a-fwere obtained by a silica gel column chromatography.
  • 47
  • [ 138-38-5 ]
  • N-(4-bromobutyl)-3-(4-fluorophenyl)-4-[4-[(4-methoxybenzyl)oxy]phenyl]-1H-pyrrol-2,5-dione [ No CAS ]
  • N-(4-(4-ethylbenzenesulfonamido)butyl)-3-(4-fluorophenyl)-4-[4-[(4-methoxybenzyl)oxy]phenyl]-1H-pyrrol-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; potassium iodide; In acetonitrile;Reflux; General procedure: To a solution of substituted acetophenone (72.4mmol) 10 in CH3CN (100mL), Br2 (11.57 g, 72.4 mmol) in CH3CN (20 mL) was addeddropwise. The reaction was stirred at room temperature overnight. Solvent wasconcentrated in vacuum and the residue was diluted with ethyl acetate (150 mL)and washed with brine. The organic layer was dried over anhydrous Na2SO4and evaporated. The resulting solid was triturated with cyclohexane (50 mL) andfiltrated to give alpha-bromoacetophenone 11as a white solid. The aqueous solution of NaN3 (4.71 g, 72 mmol) wasadded to the solution of 11 (60mmol) in CH3OH (80 mL) with stirring and cooling. After 4 h, 200 mLwater was added and a large amout of white precipitate was formed. Compound 12 was obtained by filtration. A mixture of 12 (26.3 mmol), hydrochloric acid (7.98 g, 78.8 mmol) and thecatalytic amount of Pd/C was stirred at room temperature under H2 (1atm) overnight. Solvent was separated from Pd/C by filtration through Celite.The solvent was removed and the resulting residue was triturated with ethylacetate (10 mL) and filtrated to give compound 13. A mixture of 14(29.1 mmol), EDCl (7.5 g, 39.67 mmol), HOBT (5.5 g, 39.67 mmol)and N-methylmorpholine (10.5 g, 105.80 mmol) in anhydrous CH2Cl2(50 mL) proceeded with stirring and cooling for 30 min. The reaction was addedby 13 and stirred at roomtemperature for 10 h. The white solid formed was filtrated to give part ofphenylacetamide 15. The filtrate was washed with waterand dried over anhydrous Na2SO4 and evaporated. Theresidue was chromatographed to give another part of 15. Et3N (10.55 g, 104.38 mmol) was added to asuspension of 15 (12.28 mmo) inacetic anhydride (15.65 g, 153.51 mmol) under nitrogen atmosphere at 0 C. The mixture was stirred at 75 for 4 h and concentrated in vacuum. Water and CH2Cl2were added to the residue, and the organic layer was separated, washed withbrine, dried over anhydrous Na2SO4 andconcentrated. The resulting residue was triturated with diethyl ether (20 mL)and filtrated to give 16. To asuspension of 16 (21.87 mmol) inanhydrous CH3OH (120 mL), 28% sodium methoxide in CH3OH(4.76 g, 22.97 mmol) was added slowly under nitrogen atmosphere at 0 C. Thereaction was stirred at the same temperature for 1 h and acetic acid (1.48 g,22.97 mmol) was added slowly. The mixture was concentrated in vacuum and theresidue was diluted with CH2Cl2. The organic layer waswashed with water, dried over anhydrous Na2SO4 andconcentrated in vacuum. The resulting solid was triturated with diethyl ether(30 mL) and filtrated to give 17 as a pale yellow solid. NaH (0.13 g,3.25 mmol) was added to the solution of 17(1.28 mmol) in anhydrous DMF (5 mL) at 0 C. The reaction was stirred at the sametemperature for 30 min, diluted with ethyl acetate (100 ml) and washed withwater (3 × 30 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated todryness. 18 was obtained by a silicagel column chromatography as a yellow solid. A mixture of 18 (4.96 mmol), K2CO3 (0.69 g, 4.96 mmol),TBAB (0.16 g, 0.5 mmol) and 1,4-dibromobutane (4.28 g, 19.84 mmol) in CH3CN(20 mL) was stirred at 45 C. The solvent was removed and the residue was diluted withethyl acetate (100 mL) and washed with water (3× 30 mL). Theorganic layer was dried over anhydrous Na2SO4and concentrated. Intermediate 19was obtained by a silica gel column chromatography. To a solution of 19 (0.37 mmol) in CH3CN (5mL) were added KI (0.11 g, 0.75 mmol), K2CO3 (0.093 g,0.56 mmol) and substituted aromatic sulfonamide (0.56 mmol ). The reaction wasstirred in the refluxing CH3CN overnight. The solvent wasconcentrated and the residue was diluted with ethyl acetate (50 mL) and washed withbrine. The organic layer was dried over anhydrousNa2SO4 and concentrated in vacuum followed by a silicagel column chromatography to yield compounds 20a-m.
  • 48
  • [ 141-32-2 ]
  • [ 138-38-5 ]
  • (Z)-butyl 3-(4-ethylbenzsulfoxamido)acrylate [ No CAS ]
  • 49
  • [ 138-38-5 ]
  • [ 108-88-3 ]
  • Ν-benzyl-4-ethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With iron(III) chloride; potassium carbonate; copper(l) chloride; In N,N-dimethyl-formamide; at 120℃; for 0.5h;Microwave irradiation; Green chemistry; 1 mmol of <strong>[138-38-5]4-ethylbenzenesulfonamide</strong> was added to the reaction vessel, 2 mmol of ferric chloride, 0.1 mmol of cuprous chloride, 0.01 mmol of potassium carbonate, 4 mL of toluene, dimethylformamide (DMF) 3 ml. Placed in a microwave reactor at 150 W power heating to 120 C continuous reaction 30 min. After the reaction is cold But cooled to room temperature and concentrated under reduced pressure. The product was purified by column chromatography to give a pale yellow solid in 76% yield.
  • 50
  • [ 138-38-5 ]
  • 1-(2-bromoethyl)-3-(4-fluorophenyl)-4-(4-((4-methoxybenzyl)oxy)phenyl)-1H-pyrrole-2,5-dione [ No CAS ]
  • C34H31FN2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; potassium iodide; In acetonitrile;Reflux; General procedure: To a solution of 3,4-diphenyl-1H-pyrrole-2,5-dione 4a (2.11mmol) in CH3CN (15mL), K2CO3 (2.53mmol), TBAB (0.2mmol) and 1,2-dibromoethane or 1,3-dibromopropane (8.43mmol) were added and the mixture was stirred at 45C overnight. Solvent was evaporated to dryness, water (30mL) added and the resulting mixture extracted with ethyl acetate. Collected organic layers were dried over anhydrous Na2SO4 and solvent evaporated to dryness. 5a-b was obtained by a silica gel column chromatography. K2CO3 (0.784mmol), KI (0.588mmol), substituted aromatic sulfonamide (0.588mmol) and compound 5a-b (0.392mmol) were added to 4mL CH3CN. The mixture was stirred reflux overnight, and solvent was concentrated, H2O added and the resulting mixture extracted with ethyl acetate. Collected organic layers were dried over anhydrous Na2SO4 and evaporated. 6a-h was obtained by a silica gel column chromatography. A solution of 6a-h (0.212mmol) in 2.12mL acetic acid proceeded at 90C overnight·H2O was added and the resulting solution was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and concentrated. Target compounds 7a-h were purified by the silica gel column chromatography.
  • 51
  • [ 138-38-5 ]
  • 1-(3-bromopropyl)-3-(4-fluorophenyl)-4-(4-((4-methoxybenzyl)oxy)phenyl)-1H-pyrrole-2,5-dione [ No CAS ]
  • C35H33FN2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; potassium iodide; In acetonitrile;Reflux; General procedure: To a solution of 3,4-diphenyl-1H-pyrrole-2,5-dione 4a (2.11mmol) in CH3CN (15mL), K2CO3 (2.53mmol), TBAB (0.2mmol) and 1,2-dibromoethane or 1,3-dibromopropane (8.43mmol) were added and the mixture was stirred at 45C overnight. Solvent was evaporated to dryness, water (30mL) added and the resulting mixture extracted with ethyl acetate. Collected organic layers were dried over anhydrous Na2SO4 and solvent evaporated to dryness. 5a-b was obtained by a silica gel column chromatography. K2CO3 (0.784mmol), KI (0.588mmol), substituted aromatic sulfonamide (0.588mmol) and compound 5a-b (0.392mmol) were added to 4mL CH3CN. The mixture was stirred reflux overnight, and solvent was concentrated, H2O added and the resulting mixture extracted with ethyl acetate. Collected organic layers were dried over anhydrous Na2SO4 and evaporated. 6a-h was obtained by a silica gel column chromatography. A solution of 6a-h (0.212mmol) in 2.12mL acetic acid proceeded at 90C overnight·H2O was added and the resulting solution was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and concentrated. Target compounds 7a-h were purified by the silica gel column chromatography.
  • 52
  • [ 138-38-5 ]
  • methyl 2-(4-(1-(4-bromobutyl)-4-(4-fluorophenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)phenoxy)acetate [ No CAS ]
  • C31H31FN2O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; potassium iodide; In acetonitrile;Reflux; General procedure: To a solution of 12 3,4-diphenyl-1H-pyrrole-2,5-dione 4b (4.96mmol) in 83 CH3CN (20mL), 84 K2CO3 (4.96mmol), 85 TBAB (0.5mmol) and 16 1,4-dibromobutane (19.84mmol) were added and the mixture was stirred at 45C overnight. Solvent was evaporated to dryness, 86 water (50mL) added and the resulting mixture extracted with ethyl acetate. Collected organic layers were dried over anhydrous Na2SO4 and solvent evaporated to dryness. 17 8 was obtained by a silica gel column chromatography. The solution of 88 BBr3 (1M, 9.47mmol) in anhydrous 89 CH2Cl2 was added to compound 17 8 (3.94mmol) in 20mL anhydrous CH2Cl2 under nitrogen atmosphere at -78C. The mixture was stirred at -78C for 1h. The temperature rised to 0C, 10mL 90 H2O was added and the resulting solution was stirred for 0.5h and extracted with ethyl acetate. Collected organic layers were washed with brine and dried over anhydrous Na2SO4, and solvent was evaporated to dryness to afford compound 18 9, a yellow solid with sufficient purity to be used without further purification. To a solution of 18 9 (1.86mmol) and 84 K2CO3 (2.28mmol) in 10mL 92 acetone, methyl bromoacetate was added. The reaction proceeded reflux overnight and was added 30mL 86 water. Then, the mixture was extracted with ethyl acetate and dried over anhydrous Na2SO4. The residue was purified by a silica gel column chromatography to give 93 10. K2CO3 (1.76mmol), KI (1.32mmol), substituted aromatic sulfonamide (1.32mmol) and compound 10 were added to 2mL CH3CN. The mixture was stirred reflux overnight, and solvent was concentrated, H2O (12mL) added and the resulting mixture extracted with ethyl acetate. Collected organic layers were dried over anhydrous Na2SO4 and evaporated. 11 was obtained by a silica gel column chromatography. 1M aqueous solution of LiOH (1.11mmol) was added to the solution of compound 11 (0.742mmol) in 4mL THF at -5C. The mixture was stirred at -5C until complete by TLC and adjusted to pH 5 by 1M HCl. The resulting mixture was extracted with diethyl ether, and the organic layer was wash by brine and dried over anhydrous Na2SO4. The solution was evaporated to afford compound 12. To a solution of glycylglycine methyl ester hydrochloride (0.81mmol) and DIPEA (1.62mmol) in 5mL CH3CN, 12 (0.67mmol), HOBt (0.81mmol) and EDCl (0.81mmol) were added at 0C. The mixture proceeded at 50C overnight, diluted with CH2Cl2 and washed with brine. The organic layer was dried over anhydrous Na2SO4 and evaporated. Compound 13 was obtained by the silica gel column chromatography. For the synthesis of 14a-j, Et3N (0.866mmol) and LiCl (0.94mmol) were added to the solution of compound 13 in 5mL CH3CN: H2O (95: 5) at 0C. The solution was adjusted to pH 5 by 1M HCl and evaporated by CH2Cl2. Combined organic layer was washed by brine, dried over anhydrous Na2SO4 and concentrated. The resulting residue was triturated with ethyl acetate and filtrated to give target compound 14a-j.
  • 53
  • [ 16712-69-9 ]
  • [ 138-38-5 ]
  • 4-ethyl-N-[(4-ethylphenyl)sulfonyl]benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With dmap; triethylamine; In toluene; at 70℃; for 12h; General procedure: A mixture of the appropriate arylsulfonyl chloride (11.2 mmol), the corresponding arylsulfonamide (12.3 mmol), DMAP (0.274 g, 2.24 mmol), and Et3N (1.95 mL, 14.0 mmol) in toluene (0.5 M) was kept at 70 C for 12 h (monitored by TLC). The reaction was quenched with aq 2 M HCl (30 mL) to pH 1. The mixture was extracted with EtOAc (3 × 20 mL) and the combined organic layers were dried (anhydrous MgSO4). The solvent was evaporated, and the crude product mixture was purified by recrystallization using hot CHCl3/hexane to afford the desired product.
  • 54
  • [ 91-01-0 ]
  • [ 138-38-5 ]
  • [ 574-42-5 ]
  • C21H21NO2S [ No CAS ]
  • 55
  • [ 138-38-5 ]
  • 3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]propyl 4-methylbenzenesulfonate [ No CAS ]
  • C33H33FN2O4S [ No CAS ]
  • 56
  • [ 138-38-5 ]
  • 1-(6-ethyl-1,1-dioxido-3-triethylsilanyl-2H-benzo[e][1,2]thiazin-2-yl)ethanone [ No CAS ]
  • 57
  • [ 138-38-5 ]
  • N-acetyl-4-ethyl-2-[(triisopropylsilanyl)-ethynyl]-benzenesulfonamide [ No CAS ]
  • 58
  • [ 138-38-5 ]
  • [ 108-24-7 ]
  • acetyl-(4-ethyl-benzenesulfonyl)-amine [ No CAS ]
  • 59
  • [ 138-38-5 ]
  • N-acetyl-4-ethyl-2-(4-methylphenylsulfonamido)benzenesulfonamide [ No CAS ]
  • 60
  • [ 138-38-5 ]
  • C23H26N2O7S2 [ No CAS ]
  • 62
  • [ 138-38-5 ]
  • [ 100-52-7 ]
  • 5-ethyl-3-phenylbenzo[d]isothiazole 1,1-dioxide [ No CAS ]
  • 63
  • [ 110-91-8 ]
  • [ 138-38-5 ]
  • (E)-4-ethyl-N-(morpholinomethylene)benzenesulfonamide [ No CAS ]
  • 64
  • [ 138-38-5 ]
  • 4-ethyl-N-(4-methyl-5-oxo-1,2-diphenyl-4,5-dihydro-1H-imidazol-4-yl)benzenesulfonamide [ No CAS ]
  • 65
  • [ 887144-94-7 ]
  • [ 138-38-5 ]
  • C9H10F3NO2S [ No CAS ]
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