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Chemical Structure| 13707-46-5
Chemical Structure| 13707-46-5
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Product Details of [ 13707-46-5 ]

CAS No. :13707-46-5 MDL No. :MFCD00193495
Formula : C14H12N2O4S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 304.32 Pubchem ID :-
Synonyms :

Safety of [ 13707-46-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13707-46-5 ]

* 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 [ 13707-46-5 ]

[ 13707-46-5 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 555-16-8 ]
  • [ 70-55-3 ]
  • [ 13707-46-5 ]
YieldReaction ConditionsOperation in experiment
96% With 3-methyl-1-sulfonic acid imidazolium chloride at 20℃; for 0.166667h; Ionic liquid;
95.6% With Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide In toluene for 3.5h; Heating; azeotropic removal of water;
95% With amberlyst 15 In toluene for 16h; Heating; Molecular sieve;
93% With indium(III) trichloride In benzene for 24h; Reflux;
93% With N,N,N-triethyl-N-sulfoethanammonium chloride In neat (no solvent) at 80℃; for 0.833333h;
91% With silica sulfuric acid at 90℃; for 0.75h;
90% With boron trifluoride diethyl ether complex In benzene for 12h; Reflux;
87% With tetrahydropyrrole In dichloromethane at 60℃; for 24h; Molecular sieve;
85% With cerium(III) trichloride In ethyl acetate at 50℃; for 6h;
85% With silica-supported iron oxide In toluene at 100℃; for 1h; Schlenk technique; Inert atmosphere; 2.2.4. General procedure for the synthesis of products General procedure: To a Schlenk tube filled with Fe3O4(at)MCM (15 mg) andtoluene (0.5 mL), aldehyde (0.12 mmol) and p-toluenesulfonamide(17.12 mg, 0.1 mmol) were added under nitrogen atmosphere. The reaction mixture was stirred for1 h at 100 °C. Then, the silica-coated magnetic nanoparticleswere separated using a simple magnet. The solutionof the reaction-separated systemwas transferred into around-bottomed flask. After the organic phase was evaporatedunder reduced pressure, the obtained crude productwas purified by recrystallization from ethyl acetate and nhexane,affording the pure product in high yield (up to98%).
78% With tetrahydropyrrole In dichloromethane at 60℃; for 25h;
78% With tetrahydropyrrole In dichloromethane for 25h; Molecular sieve; Reflux; General Procedure (D) for Synthesis of N-tosyl imines 3h to 3m The carbonyl derivative (1 eq.) is added in one portion to a suspension of p-toluenesulfonamide (1 eq.) in anhydrous dichloromethane (0.3 M) containing 10 mol % of pyrrolidine and the 4 Å molecular sieve (1 g/mmol). The solution is stirred for 25 hours at reflux. After total conversion, the medium is filtered through celite and the residue is washed with dichloromethane, then the solvent is evaporated under reduced pressure to provide one of imines 3h to 3m.
76% With N-(p-tolylsulfonyl)diphenylselenimide In toluene for 18h; Heating;
75% With ZnCl2/SiO2 In neat (no solvent) for 0.916667h; Heating; 3.1. General Procedure for the Synthesis of N-sulfonylImines General procedure: To a well ground mixture of sulfonamide (10 mmol), andSilzic (0.2 g, 20 mol%) in a 50 mL round-bottomed flaskconnected to a reflux condenser, aldehyde (10 mmol) wasadded and the mixture was allowed to stir at 100oC for thetimes reported in Table 2 (the reaction was monitored byTLC analysis). After the completion of the reaction, methylenechloride (20 mL) was added to the reaction mixture.Then, the solid was filtered off, the filtrate was concentrated,and the residue was subjected to short column chromatographyusing pet.ether-EtOAc (4:1) to give the pure product.The N-sulfonyl imines are known compounds and all spectroscopicdata were in agreement with literature reports [10-12, 16, 51].
66% With boron trifluoride diethyl ether complex In benzene for 16h; Heating;
65% With tetraethoxy orthosilicate at 160℃; for 5h;
63% With Amberlyst 15 In toluene for 24h; Inert atmosphere; Molecular sieve; Reflux;
50% With [bis(acetoxy)iodo]benzene; iodine at 50℃; for 24h; Inert atmosphere; 4.2.1. General Procedure for the Preparation of N-Sulfonyl Imines (2) (1H-NMR Yields) General procedure: To an oven-dried reaction tube was added aldehyde (1.25 mmol, 5 equivalents), PhI(OAc)2(0.50 mmol, 2 equivalents), sulfonamide (0.25 mmol, 1 equivalent), I2 (0.25 mmol, 1 equivalents),and CDCl3 (3 mL). The mixture was stirred at 50 °C under argon for 24 h. After 24 h, the reaction wascooled to room temperature and an internal standard was added (1,4-dimethoxybenzene, 0.25 mmol,35 mg); the mixture then was stirred for an additional 5-10 min. The percent yield was calculatedagainst the internal standard via 1H-NMR integrations of the imine C-H signal and the aromatic (4H)signal of the internal standard.
46% With Amberlyst 15 In toluene Molecular sieve; Reflux; Inert atmosphere;
35% Stage #1: 4-nitrobenzaldehdye; toluene-4-sulfonamide With formic acid; benzenesulfinic acid sodium salt In lithium hydroxide monohydrate at 20℃; for 16h; Stage #2: With Sodium hydrogenocarbonate In lithium hydroxide monohydrate at 20℃; for 2h;
22% With boron trifluoride diethyl ether complex In benzene Reflux;
20% With amberlyst-15 In toluene for 19h; Molecular sieve; Inert atmosphere; Reflux;
With aluminium(III) chloride
With anhydrous zinc chloride
In toluene Heating;
With 4 A molecular sieve; amberlite H+ resin IR-120 In toluene at 120℃; for 12h;
With toluene-4-sulfonic acid
With boron trifluoride diethyl ether complex
With titanium(IV) tetrachloride; triethylamine In dichloromethane Inert atmosphere;
With tetraethoxy orthosilicate at 160℃; Inert atmosphere;
Stage #1: 4-nitrobenzaldehdye; toluene-4-sulfonamide With formic acid In lithium hydroxide monohydrate at 20℃; Stage #2: With Sodium hydrogenocarbonate In dichloromethane; lithium hydroxide monohydrate at 20℃;
In toluene for 24h; Reflux;
With Amberlyst-15 In toluene for 14h; Molecular sieve; Dean-Stark; Reflux;
With amberlite H+ resin IR-120 In toluene at 120℃; for 12h; Dean-Stark; Molecular sieve; 1.1. General procedure for the synthesis of N-sulfonyl aldimines (1a, 1e-k)1 General procedure: A solution of the aldehyde (17 mmol) in toluene (70 mL) was placed in a round bottomed flask equipped with a Dean Stark assembly. p-Toluenesulfonamide/benzenesulfonamide (18 mmol), amberlite H+ resin IR-120 (2 g) and powdered molecular sieves (4 Å, 2 g) were added to the reaction flask and the mixture was stirred at 120 °C for 12 h, with azeotropic removal of water. After the reaction was complete (based upon the theoretical amount of water removal, and monitoring reaction by TLC), the mixture was allowed to cool at room temperature and filtered. The solvent was removed under reduced pressure and the resulting N-sulfonyl aldimines (1a, 1e-k) were further purified by crystallization from n-hexane.
With tetraethoxy orthosilicate at 160℃; for 8h; Inert atmosphere; Dean-Stark;
With tetraethoxy orthosilicate at 160℃; for 6h; Inert atmosphere;
With tetraethoxy orthosilicate
With toluene-4-sulfonic acid
With tetraethoxy orthosilicate at 160℃; for 10h;
With tetraethoxy orthosilicate at 160℃; for 5h; Inert atmosphere; Schlenk technique;
With tetrahydropyrrole In dichloromethane at 60℃; for 24h; Molecular sieve; Sealed tube;
With tetraethoxy orthosilicate at 140 - 160℃; Inert atmosphere;
With tetraethoxy orthosilicate at 160℃; General procedure for preparation of N-sulfonyl imines (2) General procedure: N-sulfonyl imines 2 were prepared according to the literature procedures.2 A mixture of aldehyde (1.0 eq.), p-toluenesufonamide (1.0 eq.) and tetraethoxysilane (1.05 eq.) was heated at 160 °C for 4-6 h, and then cooled to room temperature. The resulting mixture was crystallized with ethyl acetate and hexane (10:1 to 1:1) and the resulting solid was collected by filtration, dried in vacuum to afford N-sulfonylimines 2.
With boron trifluoride diethyl ether complex In toluene Reflux; Inert atmosphere; Dean-Stark;
With tetrahydropyrrole In dichloromethane at 60℃; for 20h; Inert atmosphere; Molecular sieve; Schlenk technique; Synthesis of N-tosylaziridinedicarboxylate substrates 1a-1n General procedure: Under argon atmosphere, the corresponding aromatic aldehyde (10 mmol, 1 equiv.), pyrrolidine (1 mmol, 0.1 equiv.) and 4Å molecular sieves (10g, 1g/mmol) were added into a solution of R1NH2 (10 mmol, 1 equiv.) in CH2Cl2 (30 mL). The mixture was stirred in a 100 mL Schlenk tube at 60 C for 20 h. Then, cooled to roon temperature, and the reaction mixture was filtered through a short pad of silica gel or Celite. The filtrate was concentrated in vacuo to get S-1a. Under argon atmosphere, NaH (11 mmol, 60% dispersion in mineral oil, 1.1 equiv) was added into solution of S-1a (10 mmol, 1 equiv.), 2-bromomalonate (11 mmol, 1.1 equiv.) in 20 mL of dry CH3CN was cooled to 0 oC. The resulting mixture was warmed up and stirred at room temperature. Upon completion (monitored by TLC), the reaction mixture was filtered through a small plug of silica gel eluted with CH2Cl2 to remove the excess NaH and resulting NaBr. After concentration in vacuo, the crude mixture was quickly purified by flash chromatography on silica gel (eluent: n-Hexane/EtOAc = 100/2 to 100/15) to afford the desired product 1a.
In ethanol at 80℃; 2.1.1 General procedure for the synthesis of N-[(R-phenyl)methylidene]-4-methylbenzenesulfonamide 3 (a-t) [28] General procedure: An equimolar quantity of corresponding aromatic aldehyde 2 (a-t) (0.01mol) and 4-methylbenzenesulfonamide (1) (1.12g, 0.01mol) in the presence of 20ml of absolute ethanol was refluxed for 5-6h. The completion of the reaction was ascertained by TLC (carbon tetrachloride/methanol, 2:1). The whole reaction mixture was transferred into a beaker containing crushed ice in boiling condition and filtered after attaining room temperature. Then the product was kept overnight, dried, and recrystallized using ethanol to get corresponding pure N-[(R-phenyl)methylidene]-4-methylbenzenesulfonamide derivatives 3 (a-t).

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[12]Current Patent Assignee: UNIVERSITY OF ROUEN NORMANDIE; UNIVERSITE DE CAEN BASSE NORMANDIE; INSTITUT NATIONAL DES SCIENCES APPLIQUEES DE ROUEN INSA; ECOLE NATIONALE SUPERIEURE D'INGENIEURS DE CAEN; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US2022/98155, 2022, A1 Location in patent: Paragraph 0408-0409; 0410-0415
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  • 2
  • [ 15029-30-8 ]
  • [ 13707-46-5 ]
  • 2,4-di(1-p-nitrophenyl-N-tosyl-aminomethyl)-5-piperidinyl-1,3-oxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% In dichloromethane at 25℃; for 15h;
  • 3
  • [ 13707-46-5 ]
  • [ 7391-40-4 ]
  • 2,4-di(1-p-nitrophenyl-N-tosyl-aminomethyl)-5-N,N-dimethylamino-1,3-oxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In dichloromethane at 25℃; for 15h;
  • 4
  • [ 74685-00-0 ]
  • [ 13707-46-5 ]
  • C23H32O6N2SSi [ No CAS ]
  • C23H32O6N2SSi [ No CAS ]
  • 5
  • [ 42201-71-8 ]
  • [ 13707-46-5 ]
  • [ 70-55-3 ]
  • [ 1010721-74-0 ]
  • 6
  • [ 570-02-5 ]
  • [ 13707-46-5 ]
  • [ 1228802-86-5 ]
  • 7
  • [ 13707-46-5 ]
  • [ 29528-28-7 ]
  • 8
  • [ 13086-06-1 ]
  • [ 24171-89-9 ]
  • [ 13707-46-5 ]
  • (E)-methyl 3-(2-(4-nitrophenyl)-5-oxo-1-tosyl-4-(tris(thiophen-2-yl)phosphoranylidene)-4,5-dihydro-1H-pyrrol-3-yl)acrylate [ No CAS ]
  • 9
  • [ 92507-97-6 ]
  • [ 13707-46-5 ]
  • (2-(3-ethyl-1-methyl-1H-imidazol-3-ium-2-yl)-1-(4-nitrophenyl)ethyl)(tosyl)amide [ No CAS ]
  • 10
  • [ 86-29-3 ]
  • [ 13707-46-5 ]
  • C28H23N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
97 %Chromat. Stage #1: Diphenylacetonitrile With C38H33BrN4O4PdS2; silver(I) acetate; potassium carbonate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Molecular sieve; Stage #2: N-tosyl-4-nitrobenzaldimine In tetrahydrofuran at 20℃; for 36h; Inert atmosphere; Schlenk technique; Molecular sieve; 1 General procedure for C-H functionalization of benzylnitrile with N-tosylaldimines catalyzed by complex 15 General procedure: Benzylnitrile (0.1mmol) was added to the mixture of AgOAc (5mol %), Cat. 15 (5mol%), K2CO3 (0.15mmol) and molecular sieves 4Å (50mg) in THF (2mL) at room temperature. The reaction mixture was stirred for 30min followed by the addition of N-tosylaldimines (0.15mmol) at the same temperature under the flow of N2. The reaction mixture was stirred for 36h and purified by column chromatography by using petroleum ether (60-80°C) and ethyl acetate (2-10%) as the eluent.
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