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CAS No. : | 51608-60-7 | MDL No. : | MFCD00964117 |
Formula : | C14H13NO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HVCKVBQOKOFBFH-UHFFFAOYSA-N |
M.W : | 259.32 | Pubchem ID : | 2755668 |
Synonyms : |
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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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With C26H36N4OS; 3-chloro-benzenecarboperoxoic acid In ethanol at -40℃; for 24 h; | General procedure: The corresponding imine (0.20 mmol), catalyst 2f (0.024 mmol) were dissolved in xylene (4.0 mL) at room temperature, and the mixture was stirred at room temperature for 5 min. Then, m-CPBA (purity 85percent, 0.24 mmol) was added at −40°C, stirring continued for the time indicated in Table 4, and the crude mixture was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=7:1) to provide the corresponding oxaziridines 3a–o. |
95% | With N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In chloroform; water at 0℃; for 2 h; | To a mixed solution of saturated aqueous sodium bicarbonate (12 ml) and chloroform (10 ml), benzyltriethylammonium chloride (290 mg, 1.27 mmol) and N-benzylidene-4-toluenesulfonamide (Reference Example 144) (3.00 g, 11.6 mmol) were added, and a solution of m-chloroperbenzoic acid (2.58 g, 12.7 mmol) in chloroform (24 ml) was added dropwise thereto at 0°C with stirring. Thereafter, the resultant was stirred at the same temperature for 2 hours, and the mixture was gradually heated to room temperature. The reaction solution was extracted with chloroform, the organic layer was washed with saturated aqueous sodium bicarbonate, an aqueous solution of 5percent sodium bisulfite, and brine, dried (over potassium carbonate), and then concentrated under a reduced pressure. Hexane was added to the residue, the resulting slurry was filtered and washed, and a title compound (3.03 g,11.0 mmol, 95percent) was obtained as a white powder. 1H-NMR (400 MHz, CDCl3) δ: 2.50 (3H, s), 5.45 (1H, s), 7.40-7.47 (7H, m), 7.93 (2H, d, J = 8.4 Hz). ESI-MS: m/z = 276 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With C26H36N4OS; 3-chloro-benzenecarboperoxoic acid; In ethanol; at -40℃; for 24h; | General procedure: The corresponding imine (0.20 mmol), catalyst 2f (0.024 mmol) were dissolved in xylene (4.0 mL) at room temperature, and the mixture was stirred at room temperature for 5 min. Then, m-CPBA (purity 85%, 0.24 mmol) was added at -40C, stirring continued for the time indicated in Table 4, and the crude mixture was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=7:1) to provide the corresponding oxaziridines 3a-o. |
95% | With N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In chloroform; water; at 0℃; for 2h; | To a mixed solution of saturated aqueous sodium bicarbonate (12 ml) and chloroform (10 ml), benzyltriethylammonium chloride (290 mg, 1.27 mmol) and N-benzylidene-4-toluenesulfonamide (Reference Example 144) (3.00 g, 11.6 mmol) were added, and a solution of m-chloroperbenzoic acid (2.58 g, 12.7 mmol) in chloroform (24 ml) was added dropwise thereto at 0C with stirring. Thereafter, the resultant was stirred at the same temperature for 2 hours, and the mixture was gradually heated to room temperature. The reaction solution was extracted with chloroform, the organic layer was washed with saturated aqueous sodium bicarbonate, an aqueous solution of 5% sodium bisulfite, and brine, dried (over potassium carbonate), and then concentrated under a reduced pressure. Hexane was added to the residue, the resulting slurry was filtered and washed, and a title compound (3.03 g,11.0 mmol, 95%) was obtained as a white powder. 1H-NMR (400 MHz, CDCl3) delta: 2.50 (3H, s), 5.45 (1H, s), 7.40-7.47 (7H, m), 7.93 (2H, d, J = 8.4 Hz). ESI-MS: m/z = 276 (M+H+). |
With sodium hypochlorite pentahydrate; In water; acetonitrile; at 20℃; for 0.5h; | 1.9743 g (12 mmol, 12 equivalents based on the substrate) of powder crystal of sodium hypochlorite pentahydrate (Nickel diazo pentahydrate, effective chlorine concentration 42%) was placed in a 50 mL recovery flask, and H 2 O 5. And dissolved in 5 mL to prepare a sodium hypochlorite aqueous solution.While confirming the pH of the aqueous solution with a pH meter, 12.5 M sodium hydroxide aqueous solution was added dropwise to adjust the pH to 14 and then cooled to 0 C. The imines (A1, 0.2590 g, 1 mmol) obtained in Synthesis Example 1 were placed in a separately prepared 30 mL flask and dissolved by adding 5 mL of water-containing acetonitrile.This acetonitrile solution was added to an aqueous sodium hypochlorite solution and stirred at 0 C. for 10 minutes.After lapse of 10 minutes, the reaction solution was brought to room temperature and further stirred for 20 minutes.After confirming that the raw material A1 (Rf = 0.45) had disappeared by thin layer chromatography (TLC, developing solvent Hexane: AcOEt = 3: 1, iodine coloration), H 2 O (50 mL) was added to the system , And extracted with AcOEt (30 mL × 3 times).The separated organic phase was washed with saturated aqueous sodium chloride solution.Anhydrous magnesium sulfate was put in the organic phase, dehydrated and dried, then it was removed by filtration operation, and the filtrate was distilled off with a rotary evaporator to give the oxaziridine compound (B1) (3-Phenyl-2-tosyl-1, 2-oxaziridine) as a white solid.As a by-product, benzaldehyde (C) was also obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With indium; trifuran-2-yl-phosphane In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With air; boron trifluoride diethyl etherate; dimethyl zinc(II) In hexane; dichloromethane at 0℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In toluene at 120℃; for 12h; Inert atmosphere; optical yield given as %de; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | Stage #1: 1-(2-methoxyphenyl)propan-1-one With titanium tetrachloride In dichloromethane at -20℃; for 0.0333333h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at -20℃; for 1h; Inert atmosphere; Stage #3: phenyl N-tosyl imine In dichloromethane at 0℃; for 12h; Inert atmosphere; optical yield given as %de; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-(2-methoxyphenyl)propan-1-one With titanium tetrachloride In dichloromethane at -20℃; for 0.0333333h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at -20℃; for 1h; Inert atmosphere; Stage #3: phenyl N-tosyl imine With titanium tetrachloride In dichloromethane at 0℃; for 12h; Inert atmosphere; optical yield given as %de; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 44 % ee 2: 82 % de | With C20H21F6N3O2 at -40℃; for 72h; Overall yield = 42 %; enantioselective reaction; | |
1: 88 % ee 2: 88 % de | With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((R)-(6-isopropoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea In dichloromethane at -40℃; for 72h; Overall yield = 59 %; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83 % ee | With (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(dimethylamino)-3,3-dimethylbutan-2-yl)thiourea at -40℃; for 72h; Overall yield = 25 %; enantioselective reaction; | |
78 % ee | With C28H32N4O2S In dichloromethane at -40℃; for 72h; Overall yield = 32 %; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 90 % ee 2: 76 % de | With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((R)-(2-(tert-butyl)-6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea In dichloromethane at -40℃; for 72h; Overall yield = 66 %; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((R)-(2-(4-fluorophenyl)-6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea In dichloromethane at -40℃; for 72h; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1-(3,5-bis(trifluoromethyl)phenyl)-3-((R)-(2-(tert-butyl)-6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea / dichloromethane / 72 h / -40 °C 2: triethylamine; silver nitrate / toluene / 20 °C | ||
Multi-step reaction with 2 steps 1: C28H32N4O2S / dichloromethane / 72 h / -40 °C 2: triethylamine; silver nitrate / toluene / 20 °C | ||
Multi-step reaction with 2 steps 1: C20H21F6N3O2 / 72 h / -40 °C 2: triethylamine; silver nitrate / toluene / 20 °C |
Multi-step reaction with 2 steps 1: 1-(3,5-bis(trifluoromethyl)phenyl)-3-((R)-(2-(4-fluorophenyl)-6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea / dichloromethane / 72 h / -40 °C 2: triethylamine; silver nitrate / toluene / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With indium(III) bromide; triethylamine; In acetonitrile; at 20℃; for 18h; | General procedure: First phenylacetylene (1 mmol) was stirred with Et3N (1 mmol) in CH3CN (5 mL) at roomtemperature. After 15-20 min, N-methyl isatin (1 mmol) and InBr3 (15 mol %)was added and the reaction mixture was stirred for 16-18 h. When N-methylisatin was completely consumed as indicated by TLC, phenyl-N-tosylmethanimine(1 mmol) was added and the reaction mixture was stirred untilthe reaction reached completion, as evidenced by TLC. Acetonitrile wasdistilled out under reduced pressure and the residue was purified by silicagel (mesh 60-120) chromatography (hexane-EtOAc) to afford thecorresponding products. Characterization data of representative compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With [{(M,SS,SS)-p-Tol-binaso}Rh(OH)]2 In water; toluene at 35℃; for 14h; Glovebox; Sealed tube; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium carbonate; In dichloromethane; at 40℃; for 4h; | General procedure: TsNBr2 (98.7 mg, 0.30 mmol) was added in one portion to a stirred solution of ether (0.20 mmol) andK2CO3 (137.9 mg, 1.0 mmol) in DCM (2.0 mL). The mixture was stirred at 40 C for 4 h, and thereaction mixture was cooled to room temperature. Then the reaction was quenched with sat. aqNa2SO3 (2.0 mL) and water (2.0 mL). The mixture was extracted with DCM (3 × 5.0 mL) and theextracts were combined, washed with brine (10.0 mL), dried over Na2SO4, filtered, and concentratedin vacuo. The residue was purified by flash column chromatography (silica gel, PE-EtOAc) to givethe corresponding product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tert-butyl peroxyacetate; copper dichloride In dimethyl sulfoxide at 25℃; for 12h; Molecular sieve; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With triphenylphosphine; In toluene; at 110℃; for 36h;Sealed tube; | General procedure: To a solution of cyanoacetylenes (0.4mmol) with N-tosylimines (0.2 mmol) in toluene (2 mL) was added Ph3P (0.2mmol). The mixture was then stirred at 110 C for 36 h in a reaction flask. Thenthe solvent was removed in vacuo and residue was purified by columnchromatography on silica gel to give the desired annulation product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-diisopropylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium tert-butylate; In tetrahydrofuran; isopropyl alcohol; at 100℃; for 18h;Inert atmosphere; Green chemistry; | Under a nitrogen atmosphere, the ligand AnIPr.HCl (5.5 mg, 5 mol%), t-BuOK (2.3 mg, 10 mol%) were sequentially added to the reaction flask.Ni (cod) 2 (5.5mg, 10mol%), THF (1.0mL), i-PrOH (1.0mL),Finally, starting materials 1b (41.3 mg, 0.2 mmol) and 2a (62 mg, 0.24 mmol) were added.Stir at 100 C for 18 hours, cool to room temperature, and dilute with ethyl acetate.Filtered through diatomaceous earth, and concentrated to obtain the target product 4a after column chromatography.White solid, yield (81%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-diisopropylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium <i>tert</i>-butylate; isopropyl alcohol In tetrahydrofuran at 100℃; for 18h; Inert atmosphere; Glovebox; Sealed tube; Green chemistry; | |
72% | With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-diisopropylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium <i>tert</i>-butylate In tetrahydrofuran; isopropyl alcohol at 100℃; for 18h; Inert atmosphere; Green chemistry; | 22 Example 22:Synthesis of (E) -N- (2,3-bis (4-ethylphenyl) -1-phenylallyl) -4-methylbenzenesulfonamide Under a nitrogen atmosphere, the ligand AnIPr.HCl (5.5 mg, 5 mol%), t-BuOK (2.3 mg, 10 mol%) were sequentially added to the reaction flask.Ni (cod) 2 (5.5mg, 10mol%), THF (1.0mL), i-PrOH (1.0mL),Finally, raw materials 1e (47 mg, 0, 2 mmol) and 2a (62 mg, 0.24 mmol) were added.Stir at 100 ° C for 18 hours, cool to room temperature, and dilute with ethyl acetate.Filtered through diatomaceous earth and concentrated to obtain the target product 4d after column chromatography.White solid, yield (72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-diisopropylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium tert-butylate; In tetrahydrofuran; isopropyl alcohol; at 100℃; for 18h;Inert atmosphere; Green chemistry; | Under a nitrogen atmosphere, the ligand AnIPr.HCl (5.5 mg, 5 mol%), t-BuOK (2.3 mg, 10 mol%) were sequentially added to the reaction flask.Ni (cod) 2 (5.5mg, 10mol%), THF (1.0mL), i-PrOH (1.0mL),Finally, 1 g (42.8 mg, 0.2 mmol) and 2a (62 mg, 0.24 mmol) of raw materials were added.Stir at 100 C for 18 hours, cool to room temperature, and dilute with ethyl acetate.Filter through diatomaceous earth and concentrate to isolate the target product 4f after column chromatography.White solid, yield (73%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-diisopropylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium tert-butylate; In tetrahydrofuran; isopropyl alcohol; at 100℃; for 18h;Inert atmosphere; Green chemistry; | Under a nitrogen atmosphere, the ligand AnIPr.HCl was sequentially added to the reaction flask.(5.5 mg, 5 mol%), t-BuOK (2.3 mg, 10 mol%), Ni (cod) 2 (5.5 mg, 10 mol%), THF (1.0 mL), i-PrOH (1.0 mL),Lastly add raw materials for 1h(62.8 mg, 0.2 mmol) and 2a (62 mg, 0.24 mmol),Stir at 100 C for 18 hours, cool to room temperature, and dilute with ethyl acetate.Filtered through diatomaceous earth, and concentrated to obtain 4 g of the target product after column chromatography.White solid, yield (53%). |
Tags: 51608-60-7 synthesis path| 51608-60-7 SDS| 51608-60-7 COA| 51608-60-7 purity| 51608-60-7 application| 51608-60-7 NMR| 51608-60-7 COA| 51608-60-7 structure
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Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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