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Product Details of [ 13909-34-7 ]

CAS No. :13909-34-7 MDL No. :MFCD00011587
Formula : C13H11NO2S Boiling Point : -
Linear Structure Formula :CH(C6H5)NSO2C6H5 InChI Key :-
M.W : 245.30 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 13909-34-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 67.71
TPSA : 54.88 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.47
Log Po/w (XLOGP3) : 2.79
Log Po/w (WLOGP) : 3.58
Log Po/w (MLOGP) : 2.93
Log Po/w (SILICOS-IT) : 2.65
Consensus Log Po/w : 2.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.44
Solubility : 0.0885 mg/ml ; 0.000361 mol/l
Class : Soluble
Log S (Ali) : -3.6
Solubility : 0.0618 mg/ml ; 0.000252 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.94
Solubility : 0.00283 mg/ml ; 0.0000115 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.77

Safety of [ 13909-34-7 ]

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 [ 13909-34-7 ]

* 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 [ 13909-34-7 ]

[ 13909-34-7 ] Synthesis Path-Downstream   1~79

  • 1
  • [ 98-10-2 ]
  • [ 100-52-7 ]
  • [ 13909-34-7 ]
YieldReaction ConditionsOperation in experiment
92% With silica sulfuric acid at 90℃; for 0.333333h;
90% With zinc(II) oxide at 110℃; for 4h;
90% With N,N,N-triethyl-N-sulfoethanammonium chloride In neat (no solvent) at 100℃; for 1h;
89% With K 10 clay; calcium carbonate; trimethyl orthoformate at 180 - 185℃; for 0.15h; Irradiation; 30 W;
89% With peroxodisulfate ion; zirconium(IV) oxide for 0.15h; microwave irradiation;
89% With molecular sieve; amberlyst resin; ammonia In toluene at 110℃; for 0.5h; 1D A solution of benzenesulphonyl chloride (10 g) in methanol (150 ml) was cooled to 0° C and ammonia gas was bubbled into the reaction mixture over a period of 15 minutes. The reaction mixture was further stirred overnight at RT. On completion, the methanol was removed under reduced pressure and water (100 ml) was added. The reaction mixture was extracted with ethyl acetate (2x100 ml). The combined organic extracts were dried over sodium sulphate. The solvent was removed under reduced pressure to give 8.6 grams of benzenesulphonamide (96%). The benzenesulphonamide (2 g) was taken together with benzaldehyde (1.34 g), amberlyst resin (0.2 g) and molecular sieves (2 g) in dry toluene (20 ml) and refluxed (110° C) for 30 minutes (till evolution of water ceases). The reaction mixture cooled to RT (without stirring) filtered through a Celite bed and washed with toluene (40 ml). Finally, the toluene was removed under reduced pressure and the obtained a residue that when kept in the refrigerator for 30 minutes yielded a solid that was triturated with n-pentane (20 ml) filtered and dried for 15-20 min to give the desired product (2.5g, 89%).
89% With amberlyst resin In toluene at 110℃; for 0.5h; Molecular sieve; Heating / reflux; A A. N-Benzylidene-benzenesulphonamideA solution of benzenesulphonyl chloride (10 g) in methanol (150 ml) was cooled to 0° C and ammonia gas was bubbled into the reaction mixture over a period of 15 minutes. The reaction mixture was further stirred overnight at RT. On completion, the methanol was removed under reduced pressure and water (100 ml) was added. The reaction mixture was extracted with ethyl acetate (2*100 ml). The combined organic extracts were dried over sodium sulphate. The solvent was removed under reduced pressure to give 8.6 grams of benzenesulphonamide (96%). The benzene- sulphonamide (2 g) was taken together with benzaldehyde (1.34 g), Amberlyst resin (0.2 g) and molecular sieves (2 g) in dry toluene (20 ml) and refluxed (110° C) for 30 minutes (till evolution of water ceases). The reaction mixture cooled to RT (without stirring) filtered through a Celite bed and washed with toluene (40 ml). Finally, the toluene was removed under reduced pressure and the obtained a residue that when kept in the refrigerator for 30 minutes yielded a solid that was triturated with n-pentane (20 ml) filtered and dried for 15-20 min to give the desired product (2.5g, 89%).
88% In toluene for 0.75h; Heating;
87% With tetrabutylammomium bromide; magnesium oxide at 110℃; for 0.133333h; Microwave irradiation; neat (no solvent);
87% With amberlyst 15 ion-exchange resin In toluene for 16h; Inert atmosphere; Molecular sieve; Reflux; Dean-Stark;
85% at 165℃;
84% With aluminum (III) chloride at 80℃; Neat (no solvent);
81% With Amberlyst 15 In toluene for 16h; Dean-Stark; Molecular sieve; Reflux;
78% With toluene-4-sulfonic acid In toluene at 23℃; Inert atmosphere; Reflux;
70% With tetrachlorosilane at 120℃; for 3.5h;
70% With cerium(III) chloride In ethyl acetate at 50℃; for 6h;
55% With Amberlyst 15 In toluene for 24h; Inert atmosphere; Molecular sieve; Reflux;
With aluminium trichloride
With formic acid; sodium 4-methylbenzenesulfinate In water at 20℃; for 20h;
With Amberlyst 15 resin In toluene for 16h; Heating / reflux; Molecular sieve; 1 A 3 I round-bottom flask is filled with 150 g of 5° molecular sieves, 2 g of Amberlyst 15 resin, 157 g of benzenesulphonamide, 1 ,65 I of toluene and 107.5 g of distilled benzaldehyde. The mixture is refluxed under argon atmosphere, distilling the reaction water for about 16 hours, then cooled to 20°C, and the suspension is filtered washing the filtrate with toluene. The toluene phase is then concentrated with a rotary EPO evaporator, obtaining an oil which solidifies when recovered with heptane.The solid product, ground in pentane until a filterable powder is obtained, is filtered and dried, obtaining 210 g of N-benzylidene benzenesulphonamide.The raw product thus obtained is refluxed in 150 ml of ethyl acetate and, when completely dissolved, it is cooled adding 400 ml of pentane.It is kept under stirring at 20°C, obtaining the crystallisation of the sulphonimine in3-4 hours.The solid is filtered and dried under reduced pressure and at 20°C to a constant weight, finally obtaining 188 g of product in the form of white crystals, which was subjected to mass spectrometry and NMR, proving to be N-benzylidene benzenesulphonamide.1H-NMR (300 MHz, CDCI3): δ (ppm) 9,04 (1 H, s); 8,00 (2H, d, J = 8 Hz); 7,90 (2H, d, J = 8Hz); 7,60 (2H, q, J = 7Hz); 7,52 (2H, t, J = 8Hz); 7,46 (2H, t, J = 8Hz).Electronic impact mass spectrometry: m/z [245] = M+, [181 ], [157], [141 ], [104]
With tetraethoxy orthosilicate at 160℃; Inert atmosphere;
With formic acid; sodium benzenesulfonate In water at 20℃; for 12h;
99 %Chromat. With potassium carbonate at 120℃; for 8h;
With formic acid; sodium benzenesulfonate In water at 20℃; for 12h;
With potassium carbonate at 120℃; for 8h; Inert atmosphere;
With magnesium sulfate; acetic acid In water; toluene
With iron(III) chloride In dichloromethane at 40℃; for 1h; Green chemistry;
With pyrrolidine In dichloromethane at 60℃; for 24h; Molecular sieve; Sealed tube;
With Amberlyst 15 ion-exchange resin for 16h; Dean-Stark; Inert atmosphere; Molecular sieve; Reflux;
With tetraethoxy orthosilicate at 160℃; Inert atmosphere; Dean-Stark;
With titanium(IV) tetraethanolate In toluene at 150℃; for 12h;
With silica-supported ZnCl2 (30%) In neat (no solvent) at 80℃; for 0.75h; 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].
With pyrrolidine
With pyrrolidine 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.
With pyrrolidine In dichloromethane at 60℃; for 20h; Inert atmosphere; Schlenk technique; Molecular sieve;
With tetraethoxy orthosilicate at 120℃;

Reference: [1]Location in patent: experimental part Zare, Abdolkarim; Hasaninejad, Alireza; Shekouhy, Mohsen; Zare, Ahmad Reza Moosavi [Organic Preparations and Procedures International, 2008, vol. 40, # 5, p. 457 - 463]
[2]Hosseini-Sarvari, Mona; Sharghi, Hashem [Phosphorus, Sulfur and Silicon and the Related Elements, 2007, vol. 182, # 9, p. 2125 - 2130]
[3]Zare, Abdolkarim; Bahrami, Firoozeh; Merajoddin, Maria; Bandari, Marzieh; Moosavi-Zare, Ahmad Reza; Zolfigol, Mohammad Ali; Hasaninejad, Alireza; Shekouhy, Mohsen; Beyzavi, Mohammad Hassan; Khakyzadeh, Vahid; Mokhlesi, Mohammad; Asgari, Zhila [Organic Preparations and Procedures International, 2013, vol. 45, # 3, p. 211 - 219]
[4]Vass, Andras; Dudas, Jozsef; Varma, Rajender S. [Tetrahedron Letters, 1999, vol. 40, # 27, p. 4951 - 4954]
[5]Jin, Tongshou; Feng, Guoliang; Yang, Mina; Li, Tongshuang [Synthetic Communications, 2004, vol. 34, # 7, p. 1277 - 1283]
[6]Current Patent Assignee: SENTINEL ONCOLOGY - WO2007/144579, 2007, A1 Location in patent: Page/Page column 51
[7]Current Patent Assignee: SENTINEL ONCOLOGY - WO2008/139152, 2008, A1 Location in patent: Page/Page column 40
[8]Jin, Tong-Shou; Yu, Mi-Jun; Liu, Li-Bin; Zhao, Ying; Li, Tong-Shuang [Synthetic Communications, 2006, vol. 36, # 16, p. 2339 - 2344]
[9]Location in patent: experimental part Hasaninejad, Alireza; Zare, Abdolkarim; Zare, Ahmad Reza Moosavi; Parhami, Abolfath; Sharghi, Hashem; Khalafi-Nezhad, Ali [Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 11, p. 2769 - 2776]
[10]Tata, Rama Rao; Fu, Chencheng; Kelley, Steven P.; Harmata, Michael [Organic Letters, 2018, vol. 20, # 18, p. 5723 - 5726]
[11]Trippe, Lukas; Nava, Analuisa; Frank, Andrea; Nubbemeyer, Udo [European Journal of Organic Chemistry, 2021, vol. 2021, # 7, p. 1156 - 1167]
[12]Location in patent: scheme or table Khoumeri, Omar; Giuglio-Tonolo, Gamal; Crozet, Maxime D.; Terme, Thierry; Vanelle, Patrice [Tetrahedron, 2011, vol. 67, # 34, p. 6173 - 6180]
[13]Martzel, Thomas; Lohier, Jean-François; Gaumont, Annie-Claude; Brière, Jean-François; Perrio, Stéphane [European Journal of Organic Chemistry, 2018, vol. 2018, # 36, p. 5069 - 5073]
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[15]Hasaninejad, Alireza; Sharghi, Hashem [Phosphorus, Sulfur and Silicon and the Related Elements, 2007, vol. 182, # 4, p. 873 - 880]
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[20]Current Patent Assignee: INDUSTRIALE CHIMICA S.R.L. - WO2006/45745, 2006, A1 Location in patent: Page/Page column 6-7
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  • 2
  • [ 13909-34-7 ]
  • [ 113548-13-3 ]
YieldReaction ConditionsOperation in experiment
95% With potassium bisulfite; potassium sulfate; potassium hydrogensulfate; potassium carbonate In water; toluene for 0.25h;
95% With Oxone; potassium carbonate In water; toluene for 0.25h; other sulfon- and sulfamimines; var. reaction time;
89% With oxone; potassium carbonate In water; toluene
84% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 3.5h; Cooling with ice; 1.6 Step 6: n-Benzyl-benzenesulfonyloxaziridine A mixture composed of n-benzylidene benzenesulfonamide (5.0 g, 20.40 mmol), benzyltriethylammonium chloride (511 mg, 2.44 mmol), chloroform (20 ml), and saturated sodium bicarbonate (20 ml) was cooled with ice, a solution of 75% m-chloroperbenzoic acid (5.64 g, 24.48 mmol) in chloroform (20 ml) was added dropwise over 30 min, and the mixture was stirred at room temperature for 3 hr. The organic layer was separated, was washed with 10% Na2SO3, saturated sodium bicarbonate, and saturated brine quentially, and was dried over potassium carbonate, and the filtrate was concentrated under reduced pressure to give the title compound as a colorless solid (4.5 g, yield 84%). 1H-NMR (400 MHz, CDCl3): δ (ppm) 8.06 (d, J = 7.2 Hz, 2H ), 7.76 (t, J = 7.2 Hz, 1H), 7.64 (t, J = 7.6 Hz, 2H), 7.47-7 .38 (m, 5H), 5.49 (s,1H); MS (ESI): m/z 261 (M-H)+.
84% With Oxone; potassium carbonate In water; toluene for 0.25h; Inert atmosphere;
76% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In chloroform at 0℃; for 0.25h;
65% With Oxone; potassium carbonate In water; toluene Inert atmosphere;
48% With N-benzyl-N,N,N-triethylammonium chloride; 3-chloro-benzenecarboperoxoic acid In chloroform at 0℃; for 1.25h; 1E N-Benzylidene-benzenesulphonamide was taken together with a saturated solution of sodium bicarbonate (12.5 ml) and N-benzyl-N,N-diethylethanaminium chloride (0.25 g) and cooled to 0° C. 3-Chloroperbenzoic acid (3 g) in chloroform (22.5 ml) was added dropwise to the reaction mixture over a period of 15 min at 0° C and stirring maintained for 1 hour. On completion, the organic layer was separated and washed with water (20 ml), 10% Na2SO3 solution (20 ml), sat. NaHCO3 (20 ml) and sat. NaCl (20 ml). The organic layer was dried over potassium carbonate, filtered and the chloroform removed under reduced pressure (below 40° C). The crude product was treated with n-Pentane (5 ml) and the resulting solid filtered. This solid was further triturated with ethyl acetate (14 ml) and then aged with n-Pentane (14 ml) overnight in the refrigerator. The resulting mixture was filtered and dried to yield the title compound (1.4 g, 48%).
With 3-chloro-benzenecarboperoxoic acid
With 3-chloro-benzenecarboperoxoic acid
1.21 g With N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In chloroform; water at 0 - 20℃; for 0.333333h; 3-Phenyl-2-phenylsulfonyl-1,2-oxaziridine (20) A mixture of benzenesulfonyl amide (1.00 g, 6.36 mmol, 1.0 equiv) and benzaldehyde dimethylacetal (949 μL, 968 mg, 6.36 mmol, 1.0 equiv) was heated to 175 °C for 1 h. The resulting solid was taken up in CH2Cl2 (1 mL) and pentane was added until a colorless precipitate forms (approx. 3 mL). The precipitate was filtered off and washed with cold pentane (3 × 2 mL). After drying overnight, the crude product was used without further purification.The crude product was dissolved in CHCl3 (10 mL) and cooled to 0 °C. Then, benzyl triethylammonium chloride (BTEAC) (106 mg, 572 μmol, 0.1 equiv) and NaHCO3 solution (10 mL) were added. Thereto, a solution of mCPBA (1.55 g, 6.29 mmol, 1.1 equiv) in CHCl3 (15 mL) was added dropwise and the mixture was stirred for 20 minutes. After warming to room temperature, the layers were separated and the organic layer was washed with water (10 mL), 10% NaSO3 solution (10 mL), water (2 × 10 mL) and NaCl solution (5 mL). The organic layer was dried (Na2SO4), filtered, and the volatile components were removed in vacuo. The residue was dissolved in CH2Cl2 (3 mL) and filtered over 10 g of silica gel. After elution with CH2Cl2 (80 mL), the solvents were removed in vacuo with a colorless solid starting to precipitate. The solid was washed with Et2O (2 mL) and dried in vacuo to give the Davis oxaziridine 20 as a light yellow solid (1.21 g, 4.62 mmol, 73% over two steps).1H NMR (400 MHz, CDCl3): δ = 5.49 (s, 1 H, H-3), 7.38-7.50 (m, 5 H, H-2”, H-3”, H-4”), 7.64 (virt. t, 3J ≈3J = 7.7 Hz, 2 H, H-3’), 7.77 (tt, 3J = 7.5 Hz, 4J = 1.3 Hz, 1 H, H-4’), 8.06 (dd, 3J = 8.6 Hz, 4J = 1.3 Hz, 1 H, H-2’).13C NMR (100 MHz, CDCl3): δ = 76.5 (d, C-3), 128.4 (d, C-2”*), 128.9 (d, C-3”*), 129.5 (d, C-2’**), 129.6 (d, C-3’**), 130.6 (s, C-1”), 131.6 (d, C-4”), 134.9 (s, C-1’), 135.1 (d, C-4’).

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[9]Davis,F.A. et al. [Journal of the Chemical Society. Chemical communications, 1977, p. 25 - 26]
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[12]Wegmann, Marcus; Bach, Thorsten [Synthesis, 2017, vol. 49, # 1, p. 209 - 217]
  • 3
  • [ 13909-34-7 ]
  • [ 113548-13-3 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In chloroform; water at 0 - 5℃; for 0.25h;
88% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 5℃; for 2h;
86% With dihydrogen peroxide; zinc(II) acetate dihydrate; sodium carbonate; carbonic acid dimethyl ester In water at 20℃; for 13h; Green chemistry;
61% With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In chloroform; water for 4h; m-chloroperbenzoic acid was added at 0 deg C over 45 min;

  • 4
  • [ 13909-34-7 ]
  • [ 54323-50-1 ]
  • N-<(3-acetyl-(R)-thiazolidin-4-yl)carbonyl>-N,N'-dicyclohexyl urea [ No CAS ]
  • (3R,4S)-5-Acetyl-2-benzenesulfonyl-3-phenyl-7-thia-2,5-diaza-spiro[3.4]octan-1-one [ No CAS ]
  • (3S,4S)-5-Acetyl-2-benzenesulfonyl-3-phenyl-7-thia-2,5-diaza-spiro[3.4]octan-1-one [ No CAS ]
  • 5
  • [ 13909-34-7 ]
  • [ 54323-50-1 ]
  • (3R,4S)-5-Acetyl-2-benzenesulfonyl-3-phenyl-7-thia-2,5-diaza-spiro[3.4]octan-1-one [ No CAS ]
  • (3S,4S)-5-Acetyl-2-benzenesulfonyl-3-phenyl-7-thia-2,5-diaza-spiro[3.4]octan-1-one [ No CAS ]
  • 6
  • [ 13909-34-7 ]
  • [ 78348-46-6 ]
  • 1,3-diphenyl-5,6,7,8-tetrahydro-imidazo[1,5-<i>a</i>]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With acetic anhydride In toluene at 80℃;
  • 7
  • [ 13909-34-7 ]
  • [ 53934-76-2 ]
  • [ 6908-67-4 ]
  • 8
  • [ 591-87-7 ]
  • [ 13909-34-7 ]
  • [ 217947-24-5 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: Allyl acetate; N-benzylidenephenylsulfonamide With tris(dibenzylideneacetone)dipalladium (0) In dimethyl sulfoxide at 20℃; for 0.166667h; Stage #2: With bis(pinacol)diborane In dimethyl sulfoxide at 60℃; for 4h;
50% With 4 A molecular sieve; hexamethyldistannane; triphenylphosphine In tetrahydrofuran at 60℃; for 9h;
  • 9
  • [ 24253-32-5 ]
  • [ 13909-34-7 ]
  • ethyl-2-(phenyl-(phenylsulfonyl)-amino-methyl)-but-3-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With bis(η3-allyl-μ-chloropalladium(II)); 4 A molecular sieve; hexamethyldistannane In tetrahydrofuran at 40℃; for 15h;
56% With {Pd(C6H3(CH2NMe2)2-2,6)Br}; 4 A molecular sieve; hexamethyldistannane In tetrahydrofuran at 40℃; for 18h;
  • 10
  • [ 127700-79-2 ]
  • [ 13909-34-7 ]
  • ethyl-2-(phenyl-(phenylsulfonyl)-amino-methyl)-but-3-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: ethyl 2-acetoxy-3-butenoate; N-benzylidenephenylsulfonamide With tris(dibenzylideneacetone)dipalladium (0) In dimethyl sulfoxide at 20℃; for 0.166667h; Stage #2: With bis(pinacol)diborane In dimethyl sulfoxide at 20℃; for 21h;
40% With 4 A molecular sieve; hexamethyldistannane; triphenylphosphine In tetrahydrofuran at 40℃; for 16h;
  • 11
  • [ 13909-34-7 ]
  • [ 24850-33-7 ]
  • [ 217947-24-5 ]
YieldReaction ConditionsOperation in experiment
95% With PCP pincer complex Pd-OCOCF3 In tetrahydrofuran at 40℃; for 16h;
69% With pincer Pd In tetrahydrofuran at 60℃; for 21h;
  • 12
  • [ 13909-34-7 ]
  • [ 43133-18-2 ]
  • N-(1,2-diphenyl-but-3-enyl)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With pincer Pd In tetrahydrofuran at 60℃; for 21h;
  • 13
  • [ 13909-34-7 ]
  • [ 63522-99-6 ]
  • N-(1,2-diphenyl-but-3-enyl)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With PCP pincer complex Pd-Cl In tetrahydrofuran at 60℃; for 21h;
  • 14
  • [ 928-49-4 ]
  • [ 13909-34-7 ]
  • C25H31NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With PMetBu2 In benzene-d6 at 100℃; for 70h;
  • 15
  • [ 13909-34-7 ]
  • [ 1066-54-2 ]
  • C23H31NO2SSi2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With PMetBu2 In benzene-d6 at 100℃; for 18h;
  • 16
  • [ 503-17-3 ]
  • [ 13909-34-7 ]
  • 1-benzenesulfonyl-3,4,5,6-tetramethyl-2-phenyl-1,2-dihydropyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With PMetBu2 In benzene-d6 at 100℃; for 48h;
  • 17
  • [ 13909-34-7 ]
  • [ 98-80-6 ]
  • [ 851-78-5 ]
YieldReaction ConditionsOperation in experiment
80% With potassium phosphate In toluene at 20℃; for 48h;
  • 18
  • [ 13909-34-7 ]
  • [ 5720-05-8 ]
  • [ 35921-73-4 ]
YieldReaction ConditionsOperation in experiment
90% With potassium phosphate In toluene at 20℃; for 48h;
  • 19
  • [ 503-17-3 ]
  • [ 13909-34-7 ]
  • (E)-N-(2-methyl-1-phenylbut-2-enyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With triphenylacetic acid; hydrogen; sodium sulfate In toluene at 60℃; for 24h;
  • 20
  • [ 13909-34-7 ]
  • [ 115224-13-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium (chiral biphenanthrol)-based pincer complex / dimethylformamide / 91 h / 20 °C 2: sodium; ammonia / tetrahydrofuran / 1.25 h / -78 °C
Multi-step reaction with 2 steps 1: palladium (chiral BINOL)-based pincer complex / dimethylsulfoxide / 96 h / 20 °C 2: sodium; ammonia / tetrahydrofuran / 1.25 h / -78 °C
  • 21
  • [ 13909-34-7 ]
  • (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In chloroform; water at 0 - 20℃; for 4h; 1 A multy-necked flask is filled with 500 ml of a saturated aqueous solution ofNaHCO3, 12.5 g of benzyltriethylammonium chloride and a solution obtained by dissolving 122 g of N-benzylidene benzenesulphonamide prepared as described above, in 380 ml of chloroform.The mixture is cooled to 0/5°C and 1 12 g of 85% m-chloroperbenzoic acid dissolved in 1 I of chloroform is added. It is stirred cold for 1 hour, then brought to a temperature of 20°C and kept under stirring for 3 hours. The organic phase is separated and washed with water, then with water and sodium sulphite, and again with water. The organic phase is then anhydrified on potassium carbonate.By filtration and concentration under reduced pressure and at a temperature lower than 40°C, a white solid is obtained which is then dissolved at 20°C with 800 ml of ethyl acetate and the obtained solution is filtered.400 ml of pentane are added to the filtered solution and it is cooled for 12 hours at0/5 °C, then filtered washing it with pentane.The solid thus prepared is dried at 20°C for 2 hours under reduced pressure, obtaining 80 g of the title product, which is kept at -18°C away from the light.1H-NMR (300 MHz, CDCI3): δ (ppm) 5,48 (1 H, s); 7,36-7,48 (5H, m); 7,60-7,64(2H, t, J = 7Hz); 7,72-7,76 (1 H, t, J = 7Hz); 8,02-8,08 (2H, d, J = 7Hz). EPO Electronic impact mass spectrometry: m/z [261 ] = M", [245], [172], [157], [141 ],[125], [105].
  • 22
  • iodo[bis(triphenylphosphine)] dioxorhenium [ No CAS ]
  • [ 13909-34-7 ]
  • [ 766-77-8 ]
  • [ 837-18-3 ]
YieldReaction ConditionsOperation in experiment
86% With trifluoroacetic acid; In methanol; benzene; EXAMPLE 2 General Procedure for Reduction of Imines In a 5 mL flask opened to the air, to a clear solution of N-benzylidenebenzene sulfonamide (100 mg, 0.408 mmol) in benzene (0.4 mL) was added dimethylphenylsilane (125 muL, 0.816 mmol). The flask was placed in a 60 C. bath and iodo[bis(triphenylphosphine)] oxorhenium(V) (18 mg, 0.021 mmol) was added. The resulting brown solution was heated at 60 C. for 2 hours. To the reaction mixture was added methanol (0.4 mL) followed by trifluoroacetic acid (35 muL), and heating continued for an additional 2 h. The crude reaction mixture was directly applied to a SiO2 column and chromatographed eluding with 1:1 hexanes:diethyl ether to afford N-phenylsulfonylbenzylamine (87 mg, 86% yield) as a slightly yellow solid.
  • 23
  • [ 13909-34-7 ]
  • [ 837-18-3 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogen;tris(2,4,6-trimethylphenyl)phosphine; tris(pentafluorophenyl)borate; In toluene; at 120℃; under 3800.26 Torr; for 8h;Product distribution / selectivity; Comparative Example - B(C6F5)-OnIy Reductive Catalysis.|0022] In the glovebox, a substrate (1 mmol) per Table 2, B(C6FO^ (26 nig, 0.05 mmol. 5 moi%) and dry toluene (4 ml) are weighed into a 100 ml round bottomed flask equipped with a scalable Teflon tap and small magnetic stirbar. The reaction is then attached to a double manifold H:/vacuum line and degassed (freeze-pump-thaw cycle x 3). The reaction is cooled to - 196C (liquid N2) and 1 atm. H2 is introduced. The flask is sealed and warmed to room temperature. The reaction is then placed in an oil bath heated to the desired temperature and stirred at 500 rpm. At 12O0C. the H2 pressure is - 5 atm. Aliquots are obtained at periodic intervals by rapidly cooling the reaction in a water bath and venting the H> pressure. Samples are taken by pipette in the glove box. The reaction is re-pressurized using the above procedure. Upon full conversion, the reaction is poured onto a 10 cm ptug of silica (200 mesh) and eluted with 2: 1 hexanes/cthyl acetate (200 ml). If the amine is not fully soluble in the reaction mixture <n="16"/>or the hexanes/ethyl acetate solvent, CH2 CI2 (3 x 5 ml) is used to wash the reaction vessel. The collected solvent is removed in vacuo to obtain the product in the time and yield shown in Table2.
94% With hydrogen;tris(pentafluorophenyl)borate; In toluene; at 120℃; under 3800.26 Torr; for 41h;Product distribution / selectivity; Comparative Example - B(C6F5)-OnIy Reductive Catalysis.|0022] In the glovebox, a substrate (1 mmol) per Table 2, B(C6FO^ (26 nig, 0.05 mmol. 5 moi%) and dry toluene (4 ml) are weighed into a 100 ml round bottomed flask equipped with a scalable Teflon tap and small magnetic stirbar. The reaction is then attached to a double manifold H:/vacuum line and degassed (freeze-pump-thaw cycle x 3). The reaction is cooled to - 196C (liquid N2) and 1 atm. H2 is introduced. The flask is sealed and warmed to room temperature. The reaction is then placed in an oil bath heated to the desired temperature and stirred at 500 rpm. At 12O0C. the H2 pressure is - 5 atm. Aliquots are obtained at periodic intervals by rapidly cooling the reaction in a water bath and venting the H> pressure. Samples are taken by pipette in the glove box. The reaction is re-pressurized using the above procedure. Upon full conversion, the reaction is poured onto a 10 cm ptug of silica (200 mesh) and eluted with 2: 1 hexanes/cthyl acetate (200 ml). If the amine is not fully soluble in the reaction mixture <n="16"/>or the hexanes/ethyl acetate solvent, CH2 CI2 (3 x 5 ml) is used to wash the reaction vessel. The collected solvent is removed in vacuo to obtain the product in the time and yield shown in Table2.
46% In toluene; at 25℃; for 48h; General procedure: To a stirred solution of aldehyde or imine (6, 1 mmol) in toluene (2 mL) were added PdO-Fe3O4 (50 mg, 1.2 mol % of Pd) and PMHS (2 mmol, 0.12 mL). The resulting mixture was stirred at room temperature during two days. The catalyst was removed by a magnet and the resulting mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to remove the solvent. The corresponding products 3a or 7 were purified by chromatography on silica gel (hexane/ethyl acetate).
  • 24
  • [ 1295-35-8 ]
  • [ 503-17-3 ]
  • [ 13909-34-7 ]
  • [ 2622-14-2 ]
  • [Ni(P(C6H11)3)(OS(C6H5)(O)NCH(C6H5)C2H2)] [ No CAS ]
  • [Ni(P(C6H11)3)((OS(C6H5)O)NCH(C6H5)C4H4)] [ No CAS ]
  • [ 947696-30-2 ]
  • 25
  • [ 1295-35-8 ]
  • [ 503-17-3 ]
  • [ 13909-34-7 ]
  • [ 2622-14-2 ]
  • [Ni(P(C6H11)3)((OS(C6H5)O)NCH(C6H5)C4H4)] [ No CAS ]
  • 26
  • [ 1295-35-8 ]
  • [ 13909-34-7 ]
  • [ 501-65-5 ]
  • [ 2622-14-2 ]
  • [ 947696-31-3 ]
  • 27
  • [ 13909-34-7 ]
  • [ 205107-96-6 ]
YieldReaction ConditionsOperation in experiment
48% With N-benzyl-N,N,N-triethylammonium chloride; sodium carbonate; 3-chloro-benzenecarboperoxoic acid In chloroform; water at 0℃; for 1.25h; B B. 2-Benzenesulphonyl-3-phenyl-oxaziridineN-Benzylidene-benzenesulphonamide was taken together with a saturated solution of sodium bicarbonate (12.5 ml) and N-benzyl-N,N-diethylethanaminium chloride (0.25 g) and cooled to 0° C. 3-Chloroperbenzoic acid (3 g) in chloroform (22.5 ml) was added dropwise to the reaction mixture over a period of 15 min at 0° C and stirring maintained for 1 hour. On completion, the organic layer was separated and washed with water (20 ml), 10% Na2SO3 solution (20 ml), sat. NaHCO3 (20 ml) and sat. NaCI (20 ml). The organic layer was dried over potassium carbonate, filtered and the chloroform removed under reduced pressure (below 40° C). The crude product was treated with n-pentane (5 ml) and the resulting solid filtered. This solid was further triturated with ethyl acetate (14 ml) and then aged with n-Pentane (14 ml) overnight in the refrigerator. The resulting mixture was filtered and dried to yield the title compound (1.4g, 48%).
  • 28
  • [ 2432-42-0 ]
  • [ 13909-34-7 ]
  • C18H21NO3S2 [ No CAS ]
  • C18H21NO3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: S-ethyl propanethioate; N-benzylidenephenylsulfonamide With magnesium bromide ethyl etherate; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane; water; ethyl acetate Inert atmosphere; optical yield given as %de;
  • 29
  • [ 1146113-17-8 ]
  • [ 13909-34-7 ]
  • (R)-N-((S)-1-hydroxy-3-methylbutan-2-yl)-2-methyl-2-((S)-phenyl(phenylsulfonamido)methyl)pentanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: (3R,7R,10S)-1-aza-3-propyl-10-isopropyl-3-methyl-8-oxa-4-thiabicyclo[5.3.0]-2-decanone With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at -78℃; for 0.25h; Stage #2: N-benzylidenephenylsulfonamide In tetrahydrofuran at -78℃; for 16h; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 23℃; for 12h;
  • 30
  • [ 1146113-20-3 ]
  • [ 13909-34-7 ]
  • N-((S)-1-hydroxy-3-methylbutan-2-yl)-2-methyl-2-(phenyl(phenylsulfonamido)methyl)pent-4-enamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: (3S,7R,10S)-1-aza-3-allyl-10-isopropyl-3-methyl-8-oxa-4-thiabicyclo[5.3.0]-2-decanone With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at -78℃; for 0.25h; Stage #2: N-benzylidenephenylsulfonamide In tetrahydrofuran at -78℃; for 16h; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 23℃; for 12h;
  • 31
  • [ 1146113-23-6 ]
  • [ 13909-34-7 ]
  • N-((S)-1-hydroxy-3-methylbutan-2-yl)-2-methyl-2-(phenyl(phenylsulfonamido)methyl)pent-4-enamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: (3R,7R,10S)-1-aza-3-allyl-10-isopropyl-3-methyl-8-oxa-4-thiabicyclo[5.3.0]-2-decanone With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at -78℃; for 0.25h; Stage #2: N-benzylidenephenylsulfonamide In tetrahydrofuran at -78℃; for 16h; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 23℃; for 12h;
  • 32
  • [ 1146113-15-6 ]
  • [ 13909-34-7 ]
  • N-((S)-1-hydroxy-3-methylbutan-2-yl)-2-methyl-2-(phenyl(phenylsulfonamido)methyl)pentanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: (3S,7R,10S)-1-aza-3-propyl-10-isopropyl-3-methyl-8-oxa-4-thiabicyclo[5.3.0]-2-decanone With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at -78℃; for 0.25h; Stage #2: N-benzylidenephenylsulfonamide In tetrahydrofuran at -78℃; for 16h; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 23℃; for 12h;
  • 33
  • [ 13909-34-7 ]
  • [ 75-24-1 ]
  • [ 119757-51-6 ]
  • (Al(CH3)C3H(C6H5)(C6H4CF3)2NSO2C6H5) [ No CAS ]
  • 34
  • [ 673-32-5 ]
  • [ 13909-34-7 ]
  • C22H21NO2S [ No CAS ]
  • C22H21NO2S [ No CAS ]
  • [ 1146-47-0 ]
YieldReaction ConditionsOperation in experiment
1: 65% 2: 13% 3: 11% With bis(1,5-cyclooctadiene)nickel(0); trimethylaluminum; tricyclohexylphosphine In hexane; toluene at 20℃; for 1.5h; Inert atmosphere;
  • 35
  • [ 928-49-4 ]
  • [ 13909-34-7 ]
  • C19H23NO2S [ No CAS ]
  • [ 1146-47-0 ]
YieldReaction ConditionsOperation in experiment
1: 59% 2: 27% With bis(1,5-cyclooctadiene)nickel(0); trimethylaluminum; tricyclohexylphosphine In hexane; toluene at 20℃; for 2.5h; Inert atmosphere;
  • 36
  • [ 2789-88-0 ]
  • [ 13909-34-7 ]
  • C29H27NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With bis(1,5-cyclooctadiene)nickel(0); trimethylaluminum; tricyclohexylphosphine In hexane; toluene at 20℃; for 6.5h; Inert atmosphere;
  • 37
  • [ 13909-34-7 ]
  • [ 501-65-5 ]
  • C27H23NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With bis(1,5-cyclooctadiene)nickel(0); trimethylaluminum; tricyclohexylphosphine In hexane; toluene at 20℃; for 1h; Inert atmosphere;
  • 38
  • [ 13909-34-7 ]
  • [ 2170-06-1 ]
  • C24H27NO2SSi [ No CAS ]
  • [ 1146-47-0 ]
YieldReaction ConditionsOperation in experiment
1: 85% 2: 7% With bis(1,5-cyclooctadiene)nickel(0); trimethylaluminum; tricyclohexylphosphine In hexane; toluene at 20℃; for 4h; Inert atmosphere;
  • 39
  • [ 13909-34-7 ]
  • [ 119757-51-6 ]
  • C29H21F6NO2S [ No CAS ]
  • 40
  • [ 851402-42-1 ]
  • [ 13909-34-7 ]
  • [ 1184294-09-4 ]
YieldReaction ConditionsOperation in experiment
97% With C21H24N2O3 In toluene at 20℃; for 15h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
  • 41
  • [ 1515-75-9 ]
  • [ 13909-34-7 ]
  • C19H19NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 3-quinuclidinol In N,N-dimethyl-formamide at 20℃; for 24h;
  • 42
  • [ 1632-76-4 ]
  • [ 13909-34-7 ]
  • [ 1266248-99-0 ]
YieldReaction ConditionsOperation in experiment
58% With 1,10-Phenanthroline; copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran at 120℃; for 4h; Inert atmosphere;
  • 43
  • [ 583-61-9 ]
  • [ 13909-34-7 ]
  • [ 1266248-94-5 ]
  • 44
  • [ 1721-26-2 ]
  • [ 13909-34-7 ]
  • [ 1266248-95-6 ]
  • 45
  • [ 84-85-5 ]
  • [ 13909-34-7 ]
  • [ 1264626-26-7 ]
YieldReaction ConditionsOperation in experiment
97% With 4-((S)-(phenanthren-9-yloxy)((2R,4S,8R)-8-vinylquinuclidin-2-yl)methyl)quinolin-6-ol In toluene at 0℃; for 48h; optical yield given as %ee; enantioselective reaction;
  • 46
  • [ 13909-34-7 ]
  • [ 604-44-4 ]
  • [ 1264626-25-6 ]
  • 48
  • [ 956478-36-7 ]
  • [ 13909-34-7 ]
  • [ 1325234-93-2 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: 2-chloro-3-(bromomethyl)-1,4-dimethoxyanthracene-9,10-dione; N-benzylidenephenylsulfonamide With Tetrakis(dimethylamino)ethylen In N,N-dimethyl-formamide at -20 - 20℃; for 9h; Stage #2: With water In N,N-dimethyl-formamide 4.3. General procedure for TDAE reaction General procedure: Into a two-necked flask equipped with a drying tube (silica gel) and a nitrogen inlet was added 10 mL of anhydrous DMF solution of 2-chloro-3-bromomethyl-1,4-dimethoxy-anthracene-9,10-dione (4) (0.4 g, 1.01 mmol) and corresponding N-(benzenesulfonyl)benzylimines 7a-i (3 equiv). The solution was stirred and maintained at this temperature for 30 min and then was added dropwise (via a syringe) the TDAE (0.15 g, 0.75 mmol). A red color immediately developed with the formation of a white fine precipitate. The solution was vigorously stirred at -20 °C for 1 h and then warmed up to rt for 8 h. After this time, TLC analysis (CH2Cl2) clearly showed that compound (4) was totally consumed. The solution was filtered (to remove the octamethyl-oxamidinium dibromide) and hydrolyzed with 70 mL of H2O. The aqueous solution was extracted with chloroform (3×40 mL), the combined organic layers washed with H2O (2×40 mL) and dried over MgSO4. Evaporation of the solvent furnished an orange viscous liquid as crude product. Purification by silica gel chromatography (CH2Cl2) and recrystallization from isopropanol gave corresponding N-substituted benzenesulfonamide derivatives (8a-i).
  • 50
  • [ 13909-34-7 ]
  • [ 1259998-90-7 ]
  • [ 1400691-52-2 ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: N-benzylidenephenylsulfonamide; 2,2,4,4,4-pentafluoro-3,3-dihydroxy-1-(naphthalen-2-yl)-butan-1-one With lithium bromide In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With triethylamine In tetrahydrofuran for 0.0833333h; N-(2,2,-Difluoro-3-(naphthalen-2-yl)-3-oxo-1-phenylpropyl)benzenesulfonamide 10 To asolution of 2,2,4,4,4-pentafluoro-3,3-dihydroxy-1-(naphthalene-2-yl)butan-1-one (30 mg, 0.090mmol) and N-benzylidenebenzenesulfonamide (28 mg, 0.11 mmol) in THF (626 μL) was addedLiBr (24 mg, 0.28 mmol) and the mixture was stirred for 10 min at rt. Next, Et3N (26 μl, 0.19mmol) was added dropwise. After 5 min, the reaction was quenched with saturated aqueous NH4Cl(3 mL) and the resultant mixture was extracted with EtOAc (2 mL × 3). The organics were driedover Na2SO4 and concentrated under reduced pressure. SiO2 flash chromatography (2:1:1hexane/Et2O/CHCl3) afforded the title compound 10 as a colorless solid in 91% yield (37 mg)
With triethylamine; lithium bromide In tetrahydrofuran at 20℃;
37 mg Stage #1: N-benzylidenephenylsulfonamide; 2,2,4,4,4-pentafluoro-3,3-dihydroxy-1-(naphthalen-2-yl)-butan-1-one With lithium bromide In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With triethylamine In tetrahydrofuran for 0.0833333h;
  • 51
  • [ 120-72-9 ]
  • [ 13909-34-7 ]
  • (S)-N-((1H-indol-3-yl)(phenyl)methyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With polystyrene-supported (R)-4-(3,3’-bis(3,5-bis(trifluoromethyl)phenyl)-2,2'-diyl hydrogen phosphate-1,1'-binaphthalen-6-yl)methoxymethyl resin In dichloromethane at 20℃; for 0.75h; enantioselective reaction;
83% With polystyrene cross-linked with divinylbenzene supported (R)-4-(3,3'-bis(3,5-bis(trifluoromethyl)phenyl)-2,2'-diylhydrogenphosphate-1,1'-binaphthalen-6-yl)methoxymethyl In dichloromethane at 20℃; for 0.75h; 2u Examples 2i-2y: Preparation of various 3-indolylmethanamine compounds General procedure: General Procedure A (examples 2i-2u and 2y): The compound of formula (VIII) (0.07 mmol, 1 equivalent), the compound of formula (VII) (amount indicated in Table 3) and the compound of formula (lllh)a obtained in Example 1 (loading indicated in Table 3) were placed in a vial and CH2CI2 (0.4 ml_, 0.16 M) was added. The reaction mixture was shaken at room temperature until Thin Layer Chromatography monitoring showed complete consumption of the starting compound of formula (VIII) and for the time indicated in Table 3. Then, the compound (lllh)a was filtered and the filtrate directly purified by column chromatography on silica gel (from CH2CI2 to CH2Cl2/EtOAc 96:4), unless otherwise stated.
  • 52
  • [ 98-10-2 ]
  • [ 100-51-6 ]
  • [ 13909-34-7 ]
  • [ 837-18-3 ]
  • [ 100-52-7 ]
YieldReaction ConditionsOperation in experiment
With Aluminium grafted mesoporous silica (Al-MCM-41) In neat (no solvent) at 180 - 220℃; for 17h; Green chemistry; General procedure: General procedure for N-alkylation of amines with alcoholsusing Al-MS
  • 53
  • [ 13909-34-7 ]
  • [ 1259998-89-4 ]
  • N-(2,2-difluoro-3-oxo-1,3-diphenylpropyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine; lithium bromide In tetrahydrofuran at 20℃; for 0.05h;
97% With triethylamine; lithium bromide In tetrahydrofuran for 0.05h; 1 4.2.4. N-(2,2-Difluoro-3-oxo-1,3-diphenylpropyl)benzenesulfonamide (10g) General procedure: To a solution of hydrate of di-ketone (0.5 mmol), imine (0.6 mmol, 1.2 equiv), and LiBr (1.5 mmol, 3.0 equiv) in THF (10 mL), was added Et3N (1.0 mmol, 2.0 equiv) dropwise. After 3 min, the reaction was quenched with saturated aqueous NH4Cl (5 mL) followed by H2O (20 mL). The organic layer was taken and the aqueous layer was extracted with EtOAc (2 × 20 mL). The combined organic layers were washed with H2O (2 × 50 mL) and brine solution (1 × 50 mL) and dried with anhydrous Na2SO4, filtered and the solvent was removed to give the crude product, which was purified by column chromatography to afford the corresponding products.
  • 54
  • [ 13909-34-7 ]
  • [ 479486-96-9 ]
  • C16H18N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In benzene at 60℃; for 24h; Inert atmosphere; Schlenk technique; General procedure: A Schlenk tube fitted with a Teflon vacuum stopcock and microstirbar was flame-heated under vacuum and refilled with Ar. NSulfonylimines(0.53 mmol) and 1.5 ml of anhydrous benzenewas added at ice bath temperature. After 20 min, 1.1 equiv ofN,N-dimethylcarbamoyl(trimethyl)silane 1 (0.59 mmol) wasadded, and the reaction mixture was stirred at 60 C until completeconsumption of the carbamoylsilane (TLC). Volatiles were thenremoved under vacuum and the residue was chromatographedusing petroleum ether-EtOAc as eluent to obtain 140.6 mg(88.9%) of N-(sulfonyl)aminoamides.
  • 55
  • [ 13909-34-7 ]
  • [ 335344-28-0 ]
  • C17H20N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In benzene at 60℃; for 20h; Inert atmosphere; Schlenk technique; Sealed tube; Cooling with ice; General procedure for the synthesis of α-(N-sulfonyl)amino-N-methoxymethyl-N-methyl- amides 3 General procedure: A Schlenk tube fitted with a Teflon vacuum stopcock and micro stirbar wasflame heated under vacuum and refilled with Ar. N-sulfonylimine 2 (0.50 mmol) andanhydrous benzene (1.5 mL) were added at ice bath temperature. After 20 min, N-methoxymethyl-N- methylcarbamoyl(trimethyl)silane 1 (0.55 mmol) was added. The sealed reaction mixture was stirred at60 °C until no carbamoylsilane 1could be detected by TLC. Volatiles were removed in vacuo to afford the crude product which was purified by columnchromatography on silica gel (petroleum ether/ethyl acetate combination) to give N-methoxymethyl-N-methyl-α-(N-sulfonyl) amino amides 3.
  • 56
  • [ 13909-34-7 ]
  • C43H41BF15N2OP [ No CAS ]
  • [ 837-18-3 ]
  • C25H42N2OP(1+)*C18HBF15(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 99% 2: 95% With hydrogen In 1,2-dichloro-ethane at 120℃; for 8h;
  • 57
  • [ 13909-34-7 ]
  • C25H42N2OP(1+)*C18HBF15(1-) [ No CAS ]
  • [ 837-18-3 ]
YieldReaction ConditionsOperation in experiment
46% In 1,2-dichloro-ethane at 150℃; for 15h;
  • 58
  • [ 13909-34-7 ]
  • [ 1864-94-4 ]
  • [ 501-65-5 ]
  • C28H21NO3S [ No CAS ]
  • 59
  • [ 1942-45-6 ]
  • [ 13909-34-7 ]
  • [ 1864-94-4 ]
  • C22H25NO3S [ No CAS ]
  • 60
  • [ 13909-34-7 ]
  • [ 5216-31-9 ]
  • [ 1864-94-4 ]
  • C28H19F2NO3S [ No CAS ]
  • 61
  • [ 13909-34-7 ]
  • [ 2132-62-9 ]
  • [ 1864-94-4 ]
  • C30H25NO5S [ No CAS ]
  • 62
  • [ 673-32-5 ]
  • [ 13909-34-7 ]
  • [ 1864-94-4 ]
  • C23H19NO3S [ No CAS ]
  • C23H19NO3S [ No CAS ]
  • 63
  • [ 13909-34-7 ]
  • [ 1864-94-4 ]
  • [ 2170-06-1 ]
  • C25H25NO3SSi [ No CAS ]
  • 64
  • [ 23056-94-2 ]
  • [ 13909-34-7 ]
  • [ 1864-94-4 ]
  • C21H21NO3S [ No CAS ]
  • 65
  • [ 13909-34-7 ]
  • [ 498-66-8 ]
  • [ 1864-94-4 ]
  • C21H21NO3S [ No CAS ]
  • 66
  • [ 13909-34-7 ]
  • [ 1219454-89-3 ]
  • N-(2,2-difluoro-1-phenyl-2-(pyridin-2-ylsulfonyl)ethyl)benzenesulfonamide [ No CAS ]
  • 67
  • [ 13909-34-7 ]
  • [ 2350-89-2 ]
  • [ 837-18-3 ]
  • C27H25NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 5% 2: 36% With (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane; (dimethoxy)methylsilane; copper diacetate; <i>tert</i>-butyl alcohol In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
  • 68
  • [ 837-18-3 ]
  • [ 13909-34-7 ]
YieldReaction ConditionsOperation in experiment
94% With N-hydroxyphthalimide; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 0.5h;
70% With di-tert-butyl peroxide; oxygen; nickel diacetate for 24h;
Multi-step reaction with 2 steps 1: potassium bromide; sodium sulfate; tert-butylhypochlorite / acetonitrile / 1 h / 20 °C 2: sodium sulfate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium carbonate / acetonitrile / 20 h / 20 °C
Stage #1: N-benzylbenzenesulfonamide With tert-butylhypochlorite; sodium sulfate; potassium bromide In acetonitrile at 20℃; for 1h; Stage #2: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In acetonitrile at 20℃; for 0.5h; Stage #3: With sodium carbonate In acetonitrile at 20℃; for 20h;

  • 69
  • [ 98-10-2 ]
  • [ 108-88-3 ]
  • [ 13909-34-7 ]
  • [ 837-18-3 ]
YieldReaction ConditionsOperation in experiment
1: 41% 2: 40% With di-tert-butyl peroxide; oxygen; nickel diacetate In neat (no solvent) at 120℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere; chemoselective reaction;
  • 70
  • [ 35802-59-6 ]
  • [ 13909-34-7 ]
  • C23H27NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With C16H23P In benzene at 20℃; for 24h; enantioselective reaction;
  • 71
  • [ 13909-34-7 ]
  • [ 1283594-68-2 ]
  • N-((3-adamantan-1-yl)-2,2-difluoro-3-oxo-1-phenylpropyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine; lithium bromide In tetrahydrofuran at 0℃; for 0.5h; N-(3-Adamantan-1-yl)-2,2-difluoro-3-oxo-1-phenylpropyl)benzenesulfonamide 12 To asolution of 1-adamantan-1-yl-2,2,4,4,4-pentafluoro-3,3-dihydroxybutan-1-one (10 mg, 0.030mmol) and N-benzylidene-1-phenylmethanamine (15 mg, 0.06 mmol) in THF (450 μL) was addedLiBr (16 mg, 0.18 mmol) and the mixture was cooled to 0 °C. Et3N (9 μl, 0.06 mmol) was addeddropwise. The reaction mixture was stirred for 30 min followed by the addition of 1 mL ofsaturated aqueous NH4Cl solution and the resultant mixture was extracted with EtOAc (10 mL ×3). The organics were dried over anhydrous Na2SO4 and concentrated under reduced pressure.SiO2 flash chromatography (5% EtOAc in hexanes) provided title compound 12 as a colorlesssolid in 80% yield (11 mg)
  • 72
  • [ 13909-34-7 ]
  • [ 10436-75-6 ]
  • [ 137768-73-1 ]
  • N-{2-[2-(N-isopropyl-N-p-tolylamino)thiazol-5-yl]-1-phenylethyl}benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In tetrahydrofuran at 0℃; for 0.333333h;
  • 73
  • [ 13909-34-7 ]
  • [ 82352-39-4 ]
  • N-(4-methyl-1-phenyl-2-tosylpenta-2,3-dien-1-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: 1-<<3-methyl-1,2-Butadienyl>sulfonyl>-4-methylbenzene With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: N-benzylidenephenylsulfonamide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
  • 74
  • [ 13909-34-7 ]
  • [ 685-87-0 ]
  • [ 1173188-96-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In acetonitrile; mineral oil at 0 - 20℃; Inert atmosphere; 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.
With sodium hydride In acetonitrile; mineral oil at 0 - 20℃; Inert atmosphere; Schlenk technique;
With sodium hydride In acetonitrile
  • 75
  • [ 28917-17-1 ]
  • [ 13909-34-7 ]
  • N-[1-phenyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)prop-2-en-1-yl]benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With 1,4-diaza-bicyclo[2.2.2]octane; acetic acid In toluene at 20℃; for 0.8h; Inert atmosphere; General Procedure for the Synthesis of Aza-Morita-Baylis-Hilman Adducts 3a-p General procedure: In a 2mL flask equipped with a magnetic stir bar, oxadiazole(0.29 mmol), imine (0.32 mmol), and DABCO (34 mg, 0.30mmol) were added sequentially. The atmosphere of the flaskwas exchanged for N2, and then toluene (0.29 mL) and aceticacid (18 L, 0.30 mmol) were added. The reaction was stirred atroom temperature, and the time was specified for each substrate.After consumption of the starting material, as determinedby TLC, the crude reaction was evaporated underreduced pressure. The residue was then purified by flash silicagel column chromatography (hexane/EtOAc = 9:1 to 7:3) toprovide the aza-MBH adduct.
  • 76
  • [ 13909-34-7 ]
  • [ 122503-21-3 ]
  • N-{2-[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-1-(4-nitrophenyl)prop-2-en-1-yl}benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With 1,4-diaza-bicyclo[2.2.2]octane; acetic acid In toluene at 20℃; for 5h; Inert atmosphere; General Procedure for the Synthesis of Aza-Morita-Baylis-Hilman Adducts 3a-p General procedure: In a 2mL flask equipped with a magnetic stir bar, oxadiazole(0.29 mmol), imine (0.32 mmol), and DABCO (34 mg, 0.30mmol) were added sequentially. The atmosphere of the flaskwas exchanged for N2, and then toluene (0.29 mL) and aceticacid (18 L, 0.30 mmol) were added. The reaction was stirred atroom temperature, and the time was specified for each substrate.After consumption of the starting material, as determinedby TLC, the crude reaction was evaporated underreduced pressure. The residue was then purified by flash silicagel column chromatography (hexane/EtOAc = 9:1 to 7:3) toprovide the aza-MBH adduct.
  • 77
  • [ 13909-34-7 ]
  • [ 122503-21-3 ]
  • N-{2-[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-1-phenylprop-2-en-1-yl}benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With 1,4-diaza-bicyclo[2.2.2]octane; acetic acid In toluene at 20℃; for 7.3h; Inert atmosphere; General Procedure for the Synthesis of Aza-Morita-Baylis-Hilman Adducts 3a-p In a 2mL flask equipped with a magnetic stir bar, oxadiazole(0.29 mmol), imine (0.32 mmol), and DABCO (34 mg, 0.30mmol) were added sequentially. The atmosphere of the flaskwas exchanged for N2, and then toluene (0.29 mL) and aceticacid (18 L, 0.30 mmol) were added. The reaction was stirred atroom temperature, and the time was specified for each substrate.After consumption of the starting material, as determinedby TLC, the crude reaction was evaporated underreduced pressure. The residue was then purified by flash silicagel column chromatography (hexane/EtOAc = 9:1 to 7:3) toprovide the aza-MBH adduct. N-{2-[3-(4-Methoxyphenyl)-1,2,4-oxadiazol-5-yl]-1-phenylprop-2-en-1-yl}benzenesulfonamide (3h)Purified by column chromatography (hexane/EtOAc = 8:2)to give 3h (100 mg, 0.22 mmol, 90%) as a white solid; mp 152-153 °C. 1H NMR (500 MHz, CDCl3): = 7.84 (d, J = 8.8 Hz, 2 H),7.70 (d, J = 7.5 Hz, 2 H), 7.42 (t, J = 7.5 Hz, 1 H), 7.31 (t, J = 7.5 Hz,2 H), 7.26-7.09 (m, 5 H), 6.90 (d, J = 8.8 Hz, 2 H), 6.22 (s, 1 H),6.18 (d, J = 9.2 Hz, 1 H), 5.81 (s, 1 H), 5.53 (d, J = 9.2 Hz, 1 H), 3.79(s, 3 H). 13C NMR (125 MHz, CDCl3): = 172.8, 168.1, 162.3,140.5, 137.9, 132.9, 132.2, 129.2, 129.0, 128.8, 128.3, 127.3,126.7, 126.3, 118.7, 114.4, 59.9, 55.6. HRMS (ESI-TOF): m/z calcdfor C24H22N3O4S+ [M + H]+: 448.1326; found: 448.1311.
  • 78
  • [ 13909-34-7 ]
  • 3-(diphenylmethyl)-5-ethenyl-1,2,4-oxadiazole [ No CAS ]
  • N-{2-[3-(diphenylmethyl)-1,2,4-oxadiazol-5-yl]-1-phenylprop-2-en-1-yl}benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With 1,4-diaza-bicyclo[2.2.2]octane; acetic acid In toluene at 20℃; for 18h; Inert atmosphere; General Procedure for the Synthesis of Aza-Morita-Baylis-Hilman Adducts 3a-p General procedure: In a 2mL flask equipped with a magnetic stir bar, oxadiazole(0.29 mmol), imine (0.32 mmol), and DABCO (34 mg, 0.30mmol) were added sequentially. The atmosphere of the flaskwas exchanged for N2, and then toluene (0.29 mL) and aceticacid (18 L, 0.30 mmol) were added. The reaction was stirred atroom temperature, and the time was specified for each substrate.After consumption of the starting material, as determinedby TLC, the crude reaction was evaporated underreduced pressure. The residue was then purified by flash silicagel column chromatography (hexane/EtOAc = 9:1 to 7:3) toprovide the aza-MBH adduct.
  • 79
  • [ 100-41-4 ]
  • [ 13909-34-7 ]
  • C21H21NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; tetrabutylammomium bromide In ethyl acetate at 20℃; for 48h; Schlenk technique; Inert atmosphere; Irradiation; General Procedure General procedure: To a 5 mL Schlenk flask, ethylbenzene 1 (2.0 equiv, 48.8 μL), benzophenoneimine2 (0.20 mmol, 36.2 mg), (n-Bu)4NBr (10 mol%, 6.5 mg) and Ir(dFCF3ppy)2(dtbbpy)PF6(2 mol%, 4.5 mg) were dissolved in AcOEt (5 mL) under a nitrogen atmosphere. Thereaction mixture was stirred and irradiated with blue LEDs (40W), with being cooled bya fan. After 48 hours, the reaction mixture was concentrated under reduced pressure toafford a mixture containing amine. The residue was purified by preparative thin-layerchromatography (PTLC) (Hexane/AcOEt = 2/1) to give amine 3 (56.8 mg, 0.198 mmol,99%) as a yellow oil.
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