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[ CAS No. 2232-08-8 ]

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CAS No. :2232-08-8MDL No. :MFCD00005285
Formula : C10H10N2O2S Boiling Point : 409.1°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :222.26Pubchem ID :75219
Synonyms :

Computed Properties of [ 2232-08-8 ]

TPSA : 60.3 H-Bond Acceptor Count : 3
XLogP3 : 1.6 H-Bond Donor Count : 0
SP3 : 0.10 Rotatable Bond Count : 2

Safety of [ 2232-08-8 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2232-08-8 ]

  • Upstream synthesis route of [ 2232-08-8 ]
  • Downstream synthetic route of [ 2232-08-8 ]

[ 2232-08-8 ] Synthesis Path-Upstream   1~16

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Reference: [1] Bulletin de la Societe Chimique de France, 1988, # 2, p. 356 - 360
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  • [ 1576-35-8 ]
Reference: [1] Letters in Organic Chemistry, 2015, vol. 12, # 9, p. 637 - 644
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  • [ 288-32-4 ]
  • [ 98-59-9 ]
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YieldReaction ConditionsOperation in experiment
89% at 20℃; for 2 h; (a) In a three-necked round bottomflask equipped with addition funnel, oil trap, magnetic stirringbar and argon atmosphere, imidazole (5.502 g, 0.081 mol) wasdissolved in 25 mL of anhyd. CH2Cl2. The solutionwas cooled to 0 Cand then 6.78 g (0.036 mol) of p-toluenesulfonyl chloride dissolvedin 25 mL of anhydrous methylene chloridewas added dropwise. Theresulting mixture was stirred during 2 h at rt and then filtered oversilica, and the remnant solid was washed with 50 mL of a hexaneeEtOAc(1:1). The filtrate was concentrated in the rotary evaporator,redissolved in 6mL of EtOAc, and induced to precipitate uponaddition of 60 mL of hexane. The resulting white solid was filteredand dried to give 7.12 g of 1-tosyl-1H-imidazol (0.032 mol, 89percentyield).
75% at 20℃; Tosyl chloride (80.27 g; 0.421 mol; 1 eq.) dissolved in 250 ml of dichloromethane is added over 4 hours to imidazole (65.08 g; 0.956 mol; 2.27 eq.) dissolved in 250 ml of dichloromethane, in a 1 litre three-necked flash equipped with a thermometer and under an inert atmosphere.
The reaction medium is left stirring overnight at ambient temperature and then filtered over celite and washed with 500 ml of an ethyl acetate/cyclohexane (1/1) mixture.
The filtrate is concentrated on a rotary evaporator and the solid residue is then taken up in 50 ml of ethyl acetate and precipitated from 500 ml of cyclohexane.
The precipitate formed is filtered off, dried, and taken up in a minimum of dichloromethane.
The organic phase is washed with water and then with a saturated sodium chloride solution.
The aqueous phase is extracted with dichloromethane.
The organic phases are combined, dried over Na2SO4 and concentrated under reduced pressure.
Finally, the residual solid is recrystallized from isopropyl ether.
After filtration and washing with ether, compound 1 is obtained with a 75percent yield.
TLC: Rf=0.6 eluent: CH2Cl2/MeOH 98/2 (v/v)
M.p.: 78° C.
1H NMR CDCl3 δ (ppm): 8 (s, 1H, H3); 7.82 (d, 2H, Hb/b', 3Ja-b=8 Hz); 7.34 (d, 2H, Hc/c', 3Jb-a=8 Hz); 7.28 (dd, 1H, 3J=1.6 Hz, 3J=1.4 Hz, H2); 7.08 (m, 1H, H3); 2.42 (s, 3H, He)
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2209 - 2218
[2] Organic Syntheses, 2000, vol. 77, p. 225 - 225
[3] Tetrahedron, 2016, vol. 72, # 3, p. 379 - 391
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 1855 - 1858
[5] Phosphorus, Sulfur and Silicon and the Related Elements, 2011, vol. 186, # 9, p. 1867 - 1875
[6] Organic Letters, 2018, vol. 20, # 3, p. 736 - 739
[7] Green Chemistry, 2014, vol. 16, # 6, p. 3117 - 3124
[8] Patent: US2007/142324, 2007, A1, . Location in patent: Page/Page column 6
[9] European Journal of Medicinal Chemistry, 1996, vol. 31, # 12, p. 1001 - 1010
[10] Tetrahedron Letters, 2007, vol. 48, # 19, p. 3445 - 3449
[11] Organic Letters, 2010, vol. 12, # 19, p. 4232 - 4235
[12] Biomacromolecules, 2010, vol. 11, # 7, p. 1710 - 1715
[13] Tetrahedron, 2011, vol. 67, # 44, p. 8515 - 8528
[14] Patent: CN105968051, 2016, A, . Location in patent: Paragraph 0017; 0019; 0020
[15] Journal of Chemistry, 2017, vol. 2017,
  • 4
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YieldReaction ConditionsOperation in experiment
98% With tert.-butylhydroperoxide; iodine In water at 20℃; for 0.0166667 h; General procedure: To a mixture of arylsulfonyl hydrazide 1 (0.5 mmol) and amine (0.75 mmol) was added TBHP (0.2 mL, 70percent wt/wt in H2O, 2.0 mmol) followed by molecular iodine (0.025 g, 0.10 mmol, 20 molpercent) at room temperature. The reaction was completed after the addition of iodine within a minute. After completion of the reaction, as indicated by TLC, the reaction mixture was diluted with ethyl acetate, and quenched with saturated sodium thiosulphate solution and extracted twice with ethyl acetate (2 × 10 mL). The organic layer was washed with water and dried over anhyd. sodium sulphate. The solvent was evaporated in vacuo to afford pure sulfonamide derivative (8–12).
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 11, p. 1232 - 1235
[2] Chinese Journal of Chemistry, 2016, vol. 34, # 4, p. 359 - 362
  • 5
  • [ 104-15-4 ]
  • [ 530-62-1 ]
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Reference: [1] Letters in Organic Chemistry, 2015, vol. 12, # 9, p. 637 - 644
  • 6
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Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 7, p. 1575 - 1582
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  • [ 536-57-2 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1980, vol. 53, # 12, p. 3678 - 3682
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Reference: [1] Bulletin of the Chemical Society of Japan, 1980, vol. 53, # 12, p. 3678 - 3682
  • 9
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Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 7, p. 2003 - 2007
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  • [ 98-59-9 ]
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Reference: [1] Phosphorus and Sulfur and the Related Elements, 1986, vol. 26, p. 321 - 326
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Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, # 7, p. 2062 - 2070
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Reference: [1] Russian Journal of Organic Chemistry, 1996, vol. 32, # 10, p. 1495 - 1500
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Reference: [1] Russian Journal of Organic Chemistry, 1996, vol. 32, # 10, p. 1495 - 1500
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  • [ 25370-91-6 ]
  • [ 67696-28-0 ]
  • [ 433-06-7 ]
  • [ 100-52-7 ]
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  • [ 100-51-6 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1986, p. 1433 - 1435
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Reference: [1] Journal of Physical Organic Chemistry, 1997, vol. 10, # 3, p. 175 - 181
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YieldReaction ConditionsOperation in experiment
45.39%
Stage #1: at 60℃; for 2 h;
Stage #2: With sodium hydroxide In water at 20℃; for 0.666667 h;
Synthesis was carried out as described in.1 In a 1L- double-necked, round-bottomed flask, β-CD (40.0 g, 35.2 mmol) was dissolved in deionized water (450 mL) by heating at 60 °C with vigorous stirring. To the resulting milky suspension, 1-(p-toluenesulfonyl)-imidazole (12 g, 54 mmol) was added. After 2 hrs stirring, a solution of sodium hydroxide (9 g, 225 mmol) in 25 mL of water was added slowly (in about 20 minutes). After further 20 minutes stirring, unreacted 1-(p-toluenesulfonyl)imidazole was separated by filtration through a sintered glass funnel. The reaction was quenched by the addition of ammonium chloride (24.1 g, 900 mmol) with swirling to dissolve all the solids. The resulting mixture was concentrated to about half of its originalvolume by blowing a stream of air over its surface. The resulting suspension was filtered througha large sintered-glass funnel and collected solid was washed with ice water (2x100 mL) andacetone (1x200 mL) and dried over CaCl2 in vacuum desiccators until constant weight. 20.63 g,16 mmol, 45.39percent.
45.39%
Stage #1: for 2 h;
Stage #2: With sodium hydroxide In water for 0.666667 h;
Synthesis was carried out as described in [1]. In a 1L- double-necked, round-bottomed flask, β-CD (40.0 g, 35.2 mmol) was dissolved in deionized water (450 mL) by heating at 60 °C with vigorous stirring. To the resulting milky suspension, 1-(p-toluenesulfonyl)-imidazole (12 g, 54 mmol) was added. After 2 hrs stirring, a solution of sodium hydroxide (9 g, 225 mmol) in 25 mL of water was added slowly (in about 20 minutes). After further 20 minutes stirring, unreacted 1-(p-toluenesulfonyl)imidazole was separated by filtration through a sintered glass funnel. The reaction was quenched by the addition of ammonium chloride (24.1 g, 900 mmol) with swirling to dissolve all the solids. The resulting mixture was concentrated to about half of its original volume by blowing a stream of air over its surface. The resulting suspension was filtered through a large sintered-glass funnel and collected solid was washed with ice water (2x100 mL) and acetone (1x200 mL) and dried over CaCl2 in vacuum desiccators until constant weight. 20.63 g, 16 mmol, 45.39percent.TLC. Rf: 0.88 (i-Pr-OH:H2O:EtOAc:NH4OH/5:5:1:1), 1-H NMR (500 MHz, DMSO-d6) δ: 2.42 (s, 3 H), 3.20-3.65 (overlap with HDO, m, 40 H), 4.15-4.23 (m, 1 H), 4.30-4.38 (m, 2 H), 4.40-4.54 (m, 2 H), 4.50 (br s, 3 H), 4.76 (br s, 2 H), 4.84 (br s, 4 H), 5.62-5.84 (m, 14 H), 7.43 (d, 2 H, J = 7.75), 7.73 (d, 2 H, J = 7.75).
40.26%
Stage #1: at 20℃; for 2 h;
Stage #2: With sodium hydroxide In water
The synthesis of mono-6-(p-toluenesulphonyl)-6-deoxy-β-cyclodextrin was carried out using a previously reportedprocedure.43,44 In a 1 L double necked round-bottomed flask,β-cyclodextrin (40.0 g, 35.2 mmol) was dissolved in deionized water(450 mL) at 60 °C with vigorous stirring. 1-(p-Toluenesulphonyl)-imidazole (12 g, 54 mmol) was added to the resulting milkysuspension at room temperature and stirred for 2 h. After that,a solution of sodium hydroxide 9 g (225 mmol, in 25 mL water)was added dropwise over 20 min. After addition of thesodium hydroxide solution, the separation of unreacted 1-(ptoluenesulphonyl)imidazole was carried out by simple filtrationusing a sintered glass funnel. Finally the reaction was quenchedby the addition of ammonium chloride (24.1 g, 900 mmol), withagitation to dissolve the added ammonium chloride. The resultingmixture was concentrated to about half of its original volume byblowing a stream of air over its surface. The resulting suspensionwas filtered using a sintered-glass funnel and the collected solidwas washed twice using 200 mL ice-cold water and 100 mL ofacetone in one portion. The collected solid was well dried overnightin a vacuum at 60 °C and kept over CaCl2 in vacuum desiccatorsyielding 18.30 g, or 40.26percent.
35.1%
Stage #1: at 20℃; for 4 h;
Stage #2: With sodium hydroxide In water for 0.166667 h;
β-Cyclodextrin (35.0 g, 30.8 mmol) was dissolved in 350 mL H2O with 1-(p-toluenesulfonyl)imidazole (8.9 g, 40.0 mmol) and stirred at 20° C. for 4 h. NaOH (50 mL, 20percent w/v) was then added to the mixture and stirred for 10 min, inducing a precipitate. The precipitate was filtered off and the filtrate was collected, then neutralized to pH 7 with 25 g NH4Cl to form another precipitate. This precipitate was collected by filtration and washed with 100 mL of H2O three times and 100 mL of acetone twice and dried overnight under vacuum. Since both mono- and ditosylate forms existed along with unreacted β-CD, an HP20 (C 18) column was run. The mixture was loaded in bulk water and eluted with water until no more β-CD-OH emerged, at which point methanol was used as eluent and fractions were collected. Fractions were confirmed via TLC using isopropanol:H2O:EtOAc:30percent NH4OH (3:2:1:1) as solvent and acid stain (20percent H2SO4) visualization. Yield: 12.3 g (35.1percent). 1H NMR (300 MHz, DMSO-D6, δ): 7.80-7.66 (d, 2H, S-Benzene), 7.50-7.33 (d, 2H, Benz-CH3), 5.93-5.48 (b, 14H, OH on C2, C3 of CD), 4.87-4.70 (s, 7H, C1H of CD), 4.63-4.08 (b, 6H, OH on C6 of CD), 3.75-3.43 (m, 28H, C2H, C3H, C4H, and C5H of CD, overlap with HDO), 3.43-3.11 (m, 14H, C6H of CD), 2.43-2.34 (s, 3H, CH3 on OTs).
28.2% at 20 - 60℃; for 6 h; In a 250-mL three-necked round-bottomed flask, bCD (5.0 g,4.4 mmol) was dissolved in 112.5 mL of water by heating to60 C under vigorous stirring.28 After cooling to room temperature,finely powdered 1-(p-toluenesulfonyl)imidazole (3.9 g, 17.7 mmol)was added to the suspension. After 6 h, a solution of sodium hydroxide (2.3 g, 56.3 mmol) in 6.3 mL of water was added over20 min. After 10 min, unreacted 1-(p-toluenesulfonyl)imidazolewas removed by filtration. To the filtrate was added ammoniumchloride (6.1 g, 112.5 mmol) to quench the reaction. The resultingmixture was concentrated by blowing a stream of air across themixture and the product began to precipitate out of the solution.The suspension was filtered, and the solid was washed with icewater and acetone. The vacuum-dried tosyl bCD was obtained in28.2percent yield. The mono-tosylated bCD was treated with an equivalentamount of sodium azide in 16 mL of water at 80 C for 5 h.29After cooling, the solution was precipitated with acetone and thenlyophilized. Lyophilized azido bCD and triphenylphosphine (PPh3)(224 mg, 848 lmol) were dissolved in DMF (8 mL) and stirred for2 h at room temperature. After adding 1.6 mL of water, the solutionwas stirred for 3 h at 90 C, and the resulting product was precipitatedwith acetone. Amino bCD was purified by cation-exchangechromatography (CM-Sephadex C25) using 0.5-M ammoniumbicarbonate as a solvent and desalted with Bio-gel P2. The productwas confirmed using 1H NMR spectra.
28.2% at 20℃; for 6 h; Tosyl -CD was obtained from the Microbial CarbohydrateResource Bank (MCRB) at Konkuk University, Korea. Tosyl -CDwas prepared according to the method in Byun (Byun, Zhong, &Bittman, 2000). In a 1 L three-necked round-bottom flask, -CD(10.0 g, 8.8 mmol) was dissolved in 250 mL of water by heating it to60C under vigorous stirring. After cooling to room temperature,finely powdered 1-(p-toluenesulfonyl)imidazole (6 g, 27 mmol)was added to the suspension. After 6 h, a solution of sodium hydrox-ide (4.5 g, 112.5 mmol) in 12.5 mL of water was added over 20 min.After 10 min, the unreacted 1-(p-toluenesulfonyl)imidazole wasseparated by filtration. Ammonium chloride (12.05 g, 225 mmol)was then added to the reaction mixture to quench the reaction.The resulting mixture was concentrated by blowing a stream of aironto the surface overnight, after which the product precipitatedfrom the solution. The suspension was filtered, and the solid waswashed with ice water and acetone twice. The vacuum-dried tosyl-CD was obtained at a 28.2percent yield.
28.2%
Stage #1: at 20℃; for 6 h;
Stage #2: With sodium hydroxide In water at 20℃; for 0.5 h;
In a 1L three-necked round-bottom flask, β-CD (10.0g, 8.8mmol) was dissolved in 250mL of water by heating it to 60°C under vigorous stirring. After cooling to room temperature, finely powdered 1-(p-toluenesulfonyl)imidazole (6g, 27mmol) was added to the suspension. After 6h, a solution of sodiumhydroxide (4.5g, 112.5mmol) in 12.5mL of water was added over 20min. After 10min, the unreacted 1-(p-toluenesulfonyl)imidazole was separated by filtration. Ammonium chloride (12.05g, 225mmol) was then added to the reaction mixture to quench the reaction. The resulting mixture was concentrated by blowing a stream of air onto the surface overnight, after which the product precipitated from the solution. The suspension was filtered, and the solid was washed with ice water and acetone twice. The vacuum-dried tosyl β-CD was obtained at a 28.2percent yield.
28%
Stage #1: at 20℃; for 6 h;
Stage #2: With sodium hydroxide In water for 0.333333 h;
General procedure: Biotin tethering to cyclooligosaccharides starts from monotosylation on the primary hydroxylgroup, but the monotosylation method of both cyclooligosaccharides slightly differed from each other.For monotosylation of β-CD, β-CD (10.0 g, 8.8 mmol) was dissolved in water (250 mL) and heated to60 °C. After cooling to room temperature, 1-(p-toluenesulfonyl) imidazole (6 g, 27 mmol) was addedand mixed for 6 h. Sodium hydroxide (4.5 g, 112.5 mmol) solution in water (12.5 mL) was addeddropwise for 20 min. After filtration, the filtrate was quenched using ammonium chloride (12.05 g,225 mmol), and the resulting mixture was subjected to air flow for drying. The precipitated productwas washed with water and acetone. The yield of monotosylated β-CD was 28percent. For monotosylatedCyS, CyS (1 g, 0.28 mmol) was dissolved in water (50 mL), and copper sulfate (1 g, 4 mmol) in water(100 mL), was added. NaOH (1 g, 25 mmol) solution in water (50 mL) was mixed and stirredfor 10 min. The suspension became dark blue, and p-toluenesulfonyl chloride (2.5 g, 13.2 mmol)dissolved in 0.1 mL of acetonitrile was added in a dropwise manner for 1 h. The suspension wasstirred at room temperature for 4 h then neutralized with ammonium chloride. After removing the precipitate, the filtrate was concentrated and desalted on a Bio-Gel P2 column. The sample wassubjected to semi-preparative HPLC (Agilent Technologies 1200 series, Santa Clara, CA, USA) on areverse-phase column (Eclipse XDB-C18, 9.4 x 250 mm, 5 μm) at room temperature. The yieldof monotosylated CyS was 25percent. Further azidation and amination were performed, as describedin our previous report [43,44]. The mono-6-amino-β-CD or mono-6-amino-CyS were dissolved inDMF and reacted with biotinamidohexanoic acid N-hydroxysuccinimide ester for 24 h at 40 °C.After acetone precipitation, the samples were desalted and lyophilized. The overall synthetic yield fromoriginal cyclooligosaccharide to biotinylated one is about 8percent. The structures of the resulting biotinylcyclooligosaccharides were analyzed by NMR spectroscopy and MALDI-TOF mass spectrometry.
21% With sodium hydroxide In water for 1 h; 25 g (0.022 mol; 1 eq.) of β-cyclodextrin (Roquette Freres SA) are suspended in 200 ml of distilled water, in a 500 ml Erlenmeyer flask, and then sodium hydroxide chips (8.8 g) are added in a single fraction.
The reaction medium becomes clear.
Compound 1 (5 g; 0.022 mol; 1 eq.) is rapidly added to the reaction medium (the tosylimidazole remains in suspension).
After one hour, the pH is acidified to pH 6 with concentrated HCl.
The white precipitate formed is filtered off and then washed with hot distilled water (2*100 ml) and with acetone (3*100 ml), and then recrystallized from water.
After filtration and washing with acetone, compound 2 is obtained with a 21percent yield.
TLC: Rf=0.4 eluent: 6percent NH4OH/EtOH/BuOH 5/5/4 (v/v/v)
M.p.: 180° C. (decomposition point between 175° C. and 210° C.)
1H NMR DMSO-d6 δ (ppm): 7.75 (d, 2H, Hb/b', 3Ja-b=9 Hz); 7.4 (d, 2H, Hc/c', 3Jb-a=9 Hz); 5.8-5.5 (m, OH); 4.8 (m, 7H, H1-CD); 4.5-4.3 (m, 2H, H6I-CD/H6'I-CD); 3.8-3.5 (m, 20H, H5-CD/H6II-VII-CD/H6II-VII-CD/H3-CD); 3.3 (m, 14H, H2-CD/H4-CD); 2.4 (s, 3H, CH3)
ESI-MS+: m/z measured at 1290.2 for [M+H]+, calculated at 1290.2 for C49H77O37S

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