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[ CAS No. 6971-74-0 ] {[proInfo.proName]}

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Chemical Structure| 6971-74-0
Chemical Structure| 6971-74-0
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Product Details of [ 6971-74-0 ]

CAS No. :6971-74-0 MDL No. :MFCD00431862
Formula : C14H13NO3S Boiling Point : -
Linear Structure Formula :- InChI Key :SGJFNRQZMRIAJP-UHFFFAOYSA-N
M.W : 275.32 Pubchem ID :81439
Synonyms :

Calculated chemistry of [ 6971-74-0 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 72.21
TPSA : 71.62 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.9
Log Po/w (XLOGP3) : 2.83
Log Po/w (WLOGP) : 3.19
Log Po/w (MLOGP) : 2.2
Log Po/w (SILICOS-IT) : 1.9
Consensus Log Po/w : 2.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.53
Solubility : 0.0806 mg/ml ; 0.000293 mol/l
Class : Soluble
Log S (Ali) : -3.99
Solubility : 0.028 mg/ml ; 0.000102 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.23
Solubility : 0.00164 mg/ml ; 0.00000594 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.23

Safety of [ 6971-74-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6971-74-0 ]

* 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 [ 6971-74-0 ]

[ 6971-74-0 ] Synthesis Path-Downstream   1~85

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YieldReaction ConditionsOperation in experiment
95% With magnetic composite Fe3O4 Diatomite earth; In tetrahydrofuran; at 50℃; for 1h; General procedure: According to the Scheme 1, 4 mmol of N-(4-Sulfamoylphenyl) acetamide was treated with acetic anhydride (4 mmol) in glacial acetic acid (10 mL). The mixture was stirred at 50C for the predetermined time. The progress of the reaction was monitored by TLC analysis. After the completion of the reaction, the precipitate was collected by filtration and washed with water. The impure precipitate was dissolved in aqueous solution of sodium carbonate (50 mL, pH=8.0) and filtered. Acetic acid was gently added to the liquor dropwise to precipitate the product (pH=5.0). The precipitate was collected by filtration to afford N-(4-acetamidophenylsulfonyl)acetamide a1 as the white solid (0.97 g, 95%). The catalytic activities of different heterogeneous catalysts were determined by reactions performed in THF using a 1:1 molar ratio of sulfonamide to acetic anhydride or benzoyl chloride. In a typical route, N-(4-sulfamoylphenyl) acetamide (4 mmol) was treated with acetic anhydride (4 mmol) in the presence of catalyst (0.1 g) in THF (10 mL). After the appropriate time, the catalyst was separated with an external magnetic field, the solvent was evaporated by rotary evaporator. The precipitate was dissolved in aqueous solution of sodium carbonate (50 mL, pH=8.0) and filtered. Acetic acid was gently added to the liquor dropwise to precipitate the product (pH=5.0). The precipitate was collected by filtration and was washed with distilled water to afford N-(4-acetamidophenylsulfonyl)acetamide as the white solid (0.95 g, 93%).
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YieldReaction ConditionsOperation in experiment
With 5Cs(1+)*H(1+)*P2W18O62(6-) = Cs5HP2W18O62; In water; at 20℃; for 1.5h;Inert atmosphere; Green chemistry; General procedure: Under nitrogen atmosphere, a mixture of sulfonamide (1 mmol), acylating agent(2 mmol) and Cs5HP2W18O62 catalyst (5 mmol %) in water (2 mL), was stirred at roomtemperature to obtain compounds (2a-j), (3a-m), (5a-f), and under reflux for (3n-r).The reaction was monitored by TLC. After completion of the reaction, the catalyst wasremoved by filtration. The filtrate was washed by water (10 mL) and extracted withEtOAc (315 mL). The combined organic layers were dried over anhydrous Na2SO4,then the solvent was evaporated in vacuum and the crude compound was purified byflash chromatography (Merck silica gel 60 H, CH2Cl2/MeOH, 9:1) to afford the corresponding products.
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  • Acetic acid (3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-{2-[benzyl-(toluene-4-sulfonyl)-amino]-1-hydroxy-ethyl}-phenoxy)-tetrahydro-pyran-3-yl ester [ No CAS ]
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  • [ 70-11-1 ]
  • N-Benzyl-N-(2-hydroxy-2-phenyl-ethyl)-4-methyl-benzenesulfonamide [ No CAS ]
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  • [ 619-41-0 ]
  • N-Benzyl-N-(2-hydroxy-2-p-tolyl-ethyl)-4-methyl-benzenesulfonamide [ No CAS ]
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  • [ 536-38-9 ]
  • N-Benzyl-N-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-4-methyl-benzenesulfonamide [ No CAS ]
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  • [ 99-73-0 ]
  • N-Benzyl-N-[2-(4-bromo-phenyl)-2-hydroxy-ethyl]-4-methyl-benzenesulfonamide [ No CAS ]
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  • [ 403-29-2 ]
  • N-Benzyl-N-[2-(4-fluoro-phenyl)-2-hydroxy-ethyl]-4-methyl-benzenesulfonamide [ No CAS ]
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  • [ 107046-12-8 ]
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  • [ 2632-13-5 ]
  • N-Benzyl-N-[2-hydroxy-2-(4-methoxy-phenyl)-ethyl]-4-methyl-benzenesulfonamide [ No CAS ]
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  • N-bromo-N-benzoyl-4-toluenesulfonamide [ No CAS ]
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  • N-[1-(1-Acetyl-2-oxo-propoxy)-1-phenyl-meth-(E)-ylidene]-4-methyl-benzenesulfonamide [ No CAS ]
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  • [ 6773-29-1 ]
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  • 2-{Phenyl-[(E)-toluene-4-sulfonylimino]-methoxy}-malonic acid dimethyl ester [ No CAS ]
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  • benzeneselenocarboxylate [ No CAS ]
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YieldReaction ConditionsOperation in experiment
90% With copper(l) iodide; methyl ethynyl ketone; In acetonitrile; at 80℃; for 4h; To a solution of benzoic acid (9a, 61?mg, 0.5?mmol), TsN3 (5a, 148?mg, 0.75?mmol) and CuI (9.6?mg, 0.05?mmol) in MeCN (3?mL) was added but-3-yn-2-one (8a, 51?mg, 0.75?mmol). After the mixture was stirred at 80?C for 4?h (monitored by TLC), the solvent was removed. The residue was purified by a flash chromatography [silica gel, 1 % MeOH and 20 % EtOAc in petroleum ether (60-90?C)] to give 124?mg (90 %) of product 11a as a white solid, mp 140-142?C (lit [19]. 148-150?C). 1H NMR (400?MHz, CDCl3) delta 9.59 (s, 1H), 8.05-8.04 (m, 2H), 7.85-7.83 (m, 2H), 7.54-7.51 (m, 1H), 7.41-7.38 (m, 2H), 7.34-7.26 (m, 2H), 2.42 (s, 3H); 13C NMR (100?MHz, CDCl3) delta 164.5, 145.2, 135.4, 133.4, 131.0, 129.6 (2C), 128.8 (2C), 128.5 (2C), 127.9 (2C), 21.6. The products 11b-11z were prepared by the similar procedure.
  • 45
  • [ 98-88-4 ]
  • 6-t-butyl-12-p-tolyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azastibocine [ No CAS ]
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YieldReaction ConditionsOperation in experiment
1.12 g (80%) AlCl3; In benzene; a. N-(4-Methylphenylsulfonyl)benzamide p-Toluenesulfonyl isocyanate (1.00 g, 5.07 mmol) was added to a reaction vessel containing AlCl3 (1.69 g, 12.68 mmol) and benzene (35 ml). The reaction mixture was stirred under N2 and at room temperature for 3.5 hours before it was poured into crushed ice (100 ml) containing conc HCL (25 ml). The resulting mixture was stirred for 10 min and partitioned with ether (100 ml). After the aqueous layer was separated, the remaining organic layer was washed with H2 O (2*50 ml) and brine (1*50 ml), dried (Na2 SO4) and concentrated in vacuo to give the crude product (1.40 g). Purification by ether trituration (200 ml) afforded 1.12 g (80%) of the product; TLC, Rf=0.68, CH2 Cl2:MeOH:HOAc (94.5:5:0.5).
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YieldReaction ConditionsOperation in experiment
68% With 2,6-dimethylpyridine; In chloroform; at 70℃; for 16h; 4.5 Acylsulfonamide (SZ5TA1)[ 0393] A solution of (TA1) (50 mg, 0.36 mmol), (SZ5) (71 mg, 0.36 mmol) and 2,6- lutidine (40 mg, 0.37 mmol) in chloroform (10 mL) was stirred at 70 C for 16 h. Chloroform (30 mL) was added to the reaction and the resulting mixture was washed sequentially with saturated copper sulfate aqueous solution (50 mL) and brine (20 mL). The organic phase was then dried over anhydrous sodium sulfate and concentrated. Product (SZ5TA1) (67 mg, 68%) was isolated after flash chromatography (DCM: MeOH = 38: 1). Rf = 0.7 (DCM: MeOH = 10: 1). 1H-NMR (250 MHz, CDC13) delta: 9.62 (s, 1H), 7.95 (d, J= 8 Hz, 2H), 7.75 (d, J= 8.0 Hz, 2H), 7.43 (t, J= 7.2 Hz, 1H), 7.32-7.22 (m, 4H), 2.32 (s, 3H) ppm. 13C-NMR (100 MHz, CDC13) delta: 164.5, 145.1, 135.4, 133.4, 129.5, 128.7, 128.5, 127.9, 127.8, 21.6 ppm. HRMS (ESI+) for[M+H]+; calculated: 276.0694, found: 276.0696 (error m/z = -0.7 ppm).
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  • PhN=IPh [ No CAS ]
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YieldReaction ConditionsOperation in experiment
96.2% Add 1.22 g (10.0 mmole) of benzoic acid and 15 mL of chloroform to a 50 mL three-necked flask and stir for 5 minutes at room temperature. Thereafter, the internal temperature was adjusted to around 5 C. by cooling with external cooling in an ice water bath, and then 1.484 g (5.0 mmole) of triphosgene and 3.036 g (30 mmole) of triethylamine were added in turn, 1.712 g (10.0 mmole) of paratoluenesulfonamide was added thereto, and the mixture was stirred for about 5 minutes. Then, the ice water bath was removed and the temperature was raised to room temperature. The mixture was stirred for about 1 hour and thin film chromatography (TLC) After confirming the completion of the reaction, the reaction solvent was distilled off under reduced pressure, and 15 mL of water was added to the resulting solid to obtain a solid form salt, which was formed by neutralization reaction of triethylamine and hydrochloric acid produced as byproducts And the desired compound acylsulfonamide is dispersed in a solid form and stirred. After filtration, the filtrate was washed with water, and the obtained solid was dried to obtain 2.65 g (yield: 96.2%) of acyl sulfoneamide as a target compound in a solid form.
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YieldReaction ConditionsOperation in experiment
78% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; In toluene; at 130℃; for 24h;Inert atmosphere; General procedure: N-Benzoylsulfonamide 1a (27.5 mg, 0.1 mmol), [RhCl2Cp*]2 (1.2 mg, 0.002 mmol), and Cu(OAc)2·H2O (40.0 mg, 0.20 mmol) were loaded in a dry vial, which was subjected to evacuation/flushing with dry argon three times. Anhydrous toluene (1.0 mL) solution of tert-butyl acrylate 2a (17.4 muL, 0.12 mmol) was syringed into the mixture, which was then stirred at 130 C for 24 h or until the starting material had been consumed as determined by TLC. Upon cooling to room temperature, all volatiles were evaporated and the residue was purified by preparative TLC (ethyl acetate/hexane 1:2) to give isoindolinone 3a in 88% yield
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  • [ 2680-03-7 ]
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  • [ 1267588-56-6 ]
YieldReaction ConditionsOperation in experiment
82% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; In toluene; at 130℃; for 24h;Inert atmosphere; General procedure: N-Benzoylsulfonamide 1a (27.5 mg, 0.1 mmol), [RhCl2Cp*]2 (1.2 mg, 0.002 mmol), and Cu(OAc)2·H2O (40.0 mg, 0.20 mmol) were loaded in a dry vial, which was subjected to evacuation/flushing with dry argon three times. Anhydrous toluene (1.0 mL) solution of tert-butyl acrylate 2a (17.4 muL, 0.12 mmol) was syringed into the mixture, which was then stirred at 130 C for 24 h or until the starting material had been consumed as determined by TLC. Upon cooling to room temperature, all volatiles were evaporated and the residue was purified by preparative TLC (ethyl acetate/hexane 1:2) to give isoindolinone 3a in 88% yield
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  • [ 1267588-22-6 ]
YieldReaction ConditionsOperation in experiment
88% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; In toluene; at 130℃; for 24h;Inert atmosphere; General procedure: N-Benzoylsulfonamide 1a (27.5 mg, 0.1 mmol), [RhCl2Cp*]2 (1.2 mg, 0.002 mmol), and Cu(OAc)2·H2O (40.0 mg, 0.20 mmol) were loaded in a dry vial, which was subjected to evacuation/flushing with dry argon three times. Anhydrous toluene (1.0 mL) solution of tert-butyl acrylate 2a (17.4 muL, 0.12 mmol) was syringed into the mixture, which was then stirred at 130 C for 24 h or until the starting material had been consumed as determined by TLC. Upon cooling to room temperature, all volatiles were evaporated and the residue was purified by preparative TLC (ethyl acetate/hexane 1:2) to give isoindolinone 3a in 88% yield
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  • C20H19NO5S [ No CAS ]
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  • C20H21NO5S [ No CAS ]
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