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CAS No. : | 24395-14-0 | MDL No. : | MFCD00499203 |
Formula : | C15H15NO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 273.35 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 | UN#: | |
Hazard Statements: | H302-H315-H319 | Packing Group: | |
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 |
---|---|---|
With boron trifluoride diethyl etherate In dichloromethane at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With gold(III) chloride; silver trifluoromethanesulfonate In nitromethane at 20℃; for 0.0333333h; | |
88% | With indium(III) triflate In dichloromethane at 20℃; for 1.5h; | |
77% | With iron(III) chloride In nitromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With indium(III) triflate In dichloromethane at 20℃; for 1.5h; | |
90% | With iron(III) chloride In nitromethane at 20℃; for 0.0333333h; | |
81% | With gold(III) chloride; silver trifluoromethanesulfonate In nitromethane at 20℃; for 0.0333333h; |
75% | With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere; | 4.3.1. Synthesis of N-(2-(3,4-dimethoxyphenyl)-2-phenylethyl)-4-methylbenzenesulfonamide (7a). Under an argon atmosphere, BF3OEt2 (0.6 mmol, 3 equiv) was added to a solution of arene 1a (41.4 mg, 0.3 mmol) and aziridine 2a (54.4 mg, 0.2 mmol) in DCE(2 mL). The mixture was stirred at room temperature for 1h. Water(10 mL) was added and the product was extracted with EtOAc(20 mL3). The combined organic phases were dried over Na2SO4and concentrated under reduced pressure. The residue was purified by flash column chromatography (petroleum ether/ethylacetate2:1) on silica gel to afford product 7a (61.6 mg, 75% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With boron trifluoride diethyl etherate In dichloromethane at 20℃; | |
60% | With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With boron trifluoride diethyl etherate In dichloromethane at 20℃; | |
49% | With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With perchloric acid In neat (no solvent) at 20℃; for 0.0833333h; Milling; | General procedure for the synthesis of compounds 3 and 5 General procedure: A mixtureof aziridine 1 (0.25 mmol), nitrile 2 or 4 (0.25 mmol) and perchloric acid(0.25 mmol) was placed in a mortar. The reaction mixture was thoroughlyground at room temperature for 5 min. After completion (TLC) the reactionmixture was diluted with a 1 : 1 water/ethyl acetate mixture (10 ml) andwashed with sodium bicarbonate (10 ml) followed by brine solution (10 ml).Then the combined organic layer was dried over anhydrous Na2SO4.Evaporation of solvent furnished the crude product which was subjectedto column chromatography using ethyl acetate-light petroleum as eluentto obtain the analytically pure product. |
51% | at 20℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With [Ag(COD)2](+)PF6(-) In 1,2-dichloro-ethane at 30 - 35℃; for 3h; Inert atmosphere; regioselective reaction; | |
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere; | 4.2. General procedure for the synthesis of tetrahydroisoquinolines General procedure: Under an argon atmosphere, BF3OEt2 (0.6 mmol) was added toa solution of arene 1 (0.3 mmol) and aziridine 2 (0.2 mmol) in DCE(2 mL). The mixture was stirred at room temperature for 1 h and then aldehyde 3 (0.4 mmol) and anhydrous MgSO4 (400 mg) were added. The mixture was stirred at 60° C for 18 h. Cooled to room temperature, water (10 mL) was added and the product was extracted with EtOAc (20 mL3). The combined organic phaseswere dried over Na2SO4 and concentrated under reduced pressure.The residue was purified by flash column chromatography (petroleumether/ethyl acetate5:1) on silica gel to afford product 4. The physical and spectra data of the compounds 4a-4ab, 5a are shown as follows. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 72h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In chlorobenzene at 100℃; for 20h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With (R)-(+)-2,2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl; tetrakis(acetonitrile)copper(I)tetrafluoroborate In m-xylene at 15℃; for 12h; Inert atmosphere; Schlenk technique; enantioselective reaction; | |
97% | With (R)-(+)-2,2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl; tetrakis(acetonitrile)copper(I)tetrafluoroborate In m-xylene at 15℃; for 12h; Inert atmosphere; Schlenk technique; | 1 Example 1 Under argon atmosphere,To a dry Schlenk tube were added sequentially tetrabutylammonium borofluoride copper (0.0025 mmol)(R) -XylBINAP (0.0015 mmol)And dry m-xylene (0.25 mL),After stirring at room temperature for 20 minutes, 1,3-dimethylindole (0.05 mmol dissolved in 0.25 mL of dry m-xylene)And 2-phenyl-N-p-toluenesulfonylimidazine (0.11 mmol),After completion of the reaction was stirred at 15 ° C for 12 hours (TLC monitoring).The reaction was quenched by the addition of saturated aqueous sodium bicarbonate (5 mL), extracted with ethyl acetate (5 mL x 3), dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure to give the crude product which was analyzed by 1H NMR for its diastereomer The proportion of dr> 20: 1, a mixed solvent of petroleum ether: ethyl acetate = 20: 1 (containing 0.5v% triethylamine) as developing solvent,The product was isolated by column chromatography (20.3 mg, yield: 97%, e.r. = 97.5:2.5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With (R)-(+)-2,2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl; tetrakis(acetonitrile)copper(I)tetrafluoroborate; In m-xylene; at 15℃; for 48h;Inert atmosphere; Schlenk technique; | Under argon atmosphere,To a dry Schlenk tube were added sequentially tetrabutylammonium borofluoride copper (0.0025 mmol)(R) -XylBINAP (0.0015 mmol)And dry m-xylene (0.25 mL),After stirring at room temperature for 20 minutes, <strong>[10075-49-7]1,3-dimethyl-5-bromoindole</strong> (0.05 mmol dissolved in 0.25 mL of dry m-xylene)And 2-phenyl-N-p-toluenesulfonylimidazine (0.11 mmol),After the reaction was stirred at 15 C for 48 hours (TLC monitoring).The reaction was quenched by the addition of saturated aqueous sodium bicarbonate (5 mL), extracted with ethyl acetate (5 mL x 3), dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure to give the crude product which was analyzed by 1H NMR for its diastereomer The proportion of dr> 20: 1, a mixed solvent of petroleum ether: ethyl acetate = 20: 1 (containing 0.5v% triethylamine) as developing solvent,The product was isolated by column chromatography (23.7 mg, yield: 94%, e.r. = 97.5: 2.5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / toluene / 0.25 h / 20 - 90 °C / Inert atmosphere 2: copper / toluene; N,N-dimethyl-formamide / 7 h / 120 - 130 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In toluene at 20 - 90℃; for 0.25h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 2-pyridinealdoxime In N,N-dimethyl-formamide at 40℃; for 7h; regioselective reaction; | Synthesis of compounds 4; general procedure General procedure: A mixture of 2-pyridinecarboxaldehyde oxime (20 mol%, 24 mg) and CS2 or a thicyanate (1-2 mmol) in DMF (3 mL) was heated to 40 °C. Aziridine (1 mmol) was then added to the resulting mixture in one portion. The reaction mixture was then stirred for 4-7 h at 40 °C until the substrate disappeared. Afterwards, the mixture was poured in H2O (5 mL) and the pH was adjusted to 3 by addition of concentrated HCl. The mixture was extracted with EtOAc (3 × 6 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated in vacuoto give crude products. If solid, the crude product was further purified by recrystallisation from ether. The catalyst could be recovered for another run by recrystallisation from EtOH-CH2Cl2. N- (5-Phenyl-3-tosylthiazolidin-2-ylidene)propan-2-amine (5d) The crude product was purified by recrystallisation from ether affording 0.34 g (90%) 5d. M.p. 89-91 °C; IR: ν 3034, 2989, 1654, 1563, 1488, 1324, 1119 cm-1; 1H NMR: δ 0.96 (d, 3J = 6.5 Hz, 2 Me), 2.31 (s, Me), 3.63-3.68 (m, CH), 4.30-4.35 (m, CH), 4.58-4.64 (m, CH2), 7.11 (d, 3J = 6.8, 2 CH), 7.15-7.30 (m, 3 CH), 7.41 (d, 3J = 6.4 Hz, 2 CH), 7.82 (d, 3J = 6.6 Hz, 2 CH); 13C NMR: δ 21.3 (2 Me), 23.5 (Me), 49.3 (CH), 57.9 (CH), 63.4 (CH2), 127.1 (CH), 127.6 (2 CH), 128.3 (2 CH), 129.6 (2 CH), 130.1 (2 CH), 134.1 (C), 141.4 (C), 143.5 (C), 156.2 (C); EI-MS (70 eV): m/z (%) 374 (M+, 5), 171 (45), 155 (76), 104 (51), 110 (65), 77 (100), 54 (32). Anal. calcd for C19H22N2O2S3(374.52): C, 60.93, H, 5.92; N, 7.48, S, 17.12; found: C, 61.11, H, 6.11; N, 7.64, S, 17.19%. |
52% | With tris(2,2′-bipyridine)ruthenium(II) bis(tetrafluoroborate); benzenediazonium tetrafluoroborate In 1,2-dichloro-ethane at 20℃; for 10h; Inert atmosphere; Schlenk technique; Irradiation; | General experimental procedure for synthesis of 5a-q General procedure: An 25 mL oven-dried Schlenk tube was equipped with a stirring bar, an aziridine 1 (0.5 mmol), PhN2BF4 (0.6 mmol, 1.2 eq), and Ru(bpy)3(BF4)2 (0.005 mmol, 1 mol%). The mixture was degassed by using standard Schlenk techniques with the oil pump. Then isothiocyanate 4 (1.5 mmol, 3 eq), and DCE (3 mL) were injected into the reaction tube. The reaction mixture was allowed to stir for 10 h under irradiation of 45 W CFL (FSL, YPZ220/45-S, Luminous Flux (2580Lm) at rt, the distance from the light bulb to the reaction vessel being about 5 cm. After the reaction was complete (TLC), the tot he mixture was added distilled water (10 mL) and product extracted with CH2Cl2 (3 × 30 ml) in separatory funnel. The combined the organic layers were dried (Na2SO4), the organic solution was concentrated under reduced pressure using a rotary evaporator and the residue purified by column chromatography on silica gel (200-300 mesh) (PE:EtOAc = 5-10:1) to give the pure product 5.N,5-Diphenyl-3-tosylthiazolidin-2-imine (5a). White solid, mp 129-131 °C (lit. 132-133 °C)32; 1H NMR (500 MHz, CDCl3) δ 8.00 (d, J 8.4 Hz, 2H, Ph in Ts), 7.38-7.33 (m, 7H, Ph in Ts and 5-Ph), 7.28-7.26 (m, 2H, PhN=), 7.08 (t, J 7.4 Hz,1H, PhN=), 6.81-6.79 (m, 2H, PhN=), 4.82 (dd, J 8.6, 6.5 Hz, 1H, CH2), 4.62 (dd, J 10.4, 6.5 Hz, 1H, CH2), 4.07 (dd, J 10.4, 8.6 Hz, 1H, CHS), 2.50 (s, 3H, -Me). 13C NMR (125 MHz, CDCl3) δ 152.1, 150.1, 144.9, 136.5, 134.7, 129.24, 129.20, 129.05, 128.97, 128.8, 127.5, 124.3, 120.8, 56.8, 47.0, 21.7. MS (ESI): ([M+H]+) 409.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With (S)-(+)-5,5’-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4’-bi-1,3-benzodioxole; silver hexafluoroantimonate In m-xylene at 15℃; for 20h; Inert atmosphere; Schlenk technique; stereoselective reaction; | 13 Example 13 Under an argon atmosphere,To a dry Schlenk tube was added silver hexafluoroantimonate (0.0025 mmol) in that order,(S) -DTBM-SEGPHOS (0.00375 mmol) and dry m-xylene (0.25 mL)After stirring for 30 minutes at room temperature, 2-phenyl-N-p-toluenesulfonylaziridine (0.22 mmol)And 2,4,6-trimethylaniline (0.1 mmol in 0.25 mL dry m-xylene)After completion of the reaction, the reaction was stirred at 15 ° C for 20 hours (TLC monitoring).After the completion of the reaction, the solution was addedAnd aqueous sodium hydrogencarbonate (5 mL) to terminate the reaction,Extraction with ethyl acetate (5 mL x 3)Dried over anhydrous magnesium sulfate,The solvent was removed under reduced pressure to give the crude product,The mixture of petroleum ether and ethyl acetate (20: 1) (containing 0.5 v% triethylamine)The product was isolated by silica gel column chromatography on 300-400 mesh,The enantiomeric ratio (e.r.) was determined by chiral stationary phaseHPLC: yield: 38.8 mg, yield: 95%, e.r. = 97.5: 2.5. |
95% | With silver hexafluoroantimonate; (S)-DTBM-SEGPHOS In m-xylene at 15℃; for 20h; Inert atmosphere; Glovebox; Schlenk technique; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With (S)-(+)-5,5’-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4’-bi-1,3-benzodioxole; silver hexafluoroantimonate In m-xylene at 15℃; for 5h; Inert atmosphere; Schlenk technique; stereoselective reaction; | 19 Example 19 Under an argon atmosphere,To a dry Schlenk tube was added silver hexafluoroantimonate (0.0025 mmol) in that order,(S) -DTBM-SEGPHOS (0.00375 mmol) and dry m-xylene (0.25 mL)After stirring for 30 minutes at room temperature, 2-phenyl-N-p-toluenesulfonylaziridine (0.22 mmol)And indoline (0.1 mmol in 0.25 mL dry m-xylene)After completion, the reaction was stirred at 15 ° C for 5 hours (TLC monitoring).After completion of the reaction, the reaction was terminated by addition of saturated aqueous sodium hydrogencarbonate solution (5 mL)Extraction with ethyl acetate (5 mL x 3)Dried over anhydrous magnesium sulfate,The solvent was removed under reduced pressure to give the crude product,The mixture of petroleum ether and ethyl acetate (20: 1) (containing 0.5 v% triethylamine)The product was isolated by silica gel column chromatography on 300-400 mesh,The enantiomeric ratio (e.r.) was determined by HPLC on a chiral stationary phase,Yield: 38.5 mg, Yield: 98%, e.r. = 97: 3. |
98% | With silver hexafluoroantimonate; (S)-DTBM-SEGPHOS In m-xylene at 15℃; for 5h; Inert atmosphere; Glovebox; Schlenk technique; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With chloro(triphenylphosphine)gold(I); silver trifluoromethanesulfonate In dichloromethane at 0℃; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: 2-(3-iodo-phenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane; N-(p-tolylsulfonyl)-2-phenylaziridine With manganese; sodium iodide In tetrahydrofuran Inert atmosphere; Glovebox; Stage #2: With chloro-trimethyl-silane; (1,2-dimethoxyethane)dichloronickel(II); (4R,4'R)-4,4'-di(heptan-4-yl)-4,4',5,5'-tetrahydro-2,2'-bioxazole In tetrahydrofuran at -10℃; for 72h; Inert atmosphere; Sealed tube; enantioselective reaction; | |
63% | With manganese; chloro-trimethyl-silane; (1,2-dimethoxyethane)dichloronickel(II); (4S,4'S)-(4,4'-diheptan-4-yl)-4,4',5,5'-tetrahydro-2,2'-bioxazole; sodium iodide In tetrahydrofuran at -10℃; for 72h; Sealed tube; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: 2-(3-iodo-phenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane; N-(p-tolylsulfonyl)-2-phenylaziridine With manganese In N,N-dimethyl acetamide at 23℃; Inert atmosphere; Glovebox; Stage #2: With (1,2-dimethoxyethane)dichloronickel(II); 2,6-bis(pyrazole)pyridine In N,N-dimethyl acetamide at 23℃; for 18h; Inert atmosphere; Sealed tube; | |
55% | With manganese; (1,2-dimethoxyethane)dichloronickel(II); 2,6-bis(pyrazole)pyridine In N,N-dimethyl acetamide at 20℃; for 18h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: N-(p-tolylsulfonyl)-2-phenylaziridine; 2,5-dimethyl-N-methylaniline With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 60℃; for 1h; Stage #2: With tert.-butylhydroperoxide In 1,2-dichloro-ethane at 60℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77.5% | With tris(2,2′-bipyridine)ruthenium(II) bis(tetrafluoroborate); benzenediazonium tetrafluoroborate In 1,2-dichloro-ethane at 20℃; for 10h; Schlenk technique; Inert atmosphere; Irradiation; | 10 Example 10 In a 25 mL Schlenk tube,In turn, 0.3 mmol of R1 is hydrogen,R2 is a saturated aziridine of phenyl,0.006 mmol Ru (bpy) 3 (BF4) 2,0.9 mmol PhN2BF4,Nitrogen vacuum three times,4mL anhydrous 1,2-dichloroethane was added under nitrogen atmosphere,0.3 mmol of benzyl isothiocyanate,In the 30W home with white light irradiation at room temperature stirring 10h.After completion of the reaction, purification by column chromatography (column chromatography developing solvent ethyl acetate / petroleum ether = 1: 10-20) afforded N- (benzyl) -5-phenyl-3-p-methylbenzenesulfonylthiazole -2-imine 98.1 mg, yield 77.5%. |
48% | With tris(2,2′-bipyridine)ruthenium(II) bis(tetrafluoroborate); benzenediazonium tetrafluoroborate In 1,2-dichloro-ethane at 20℃; for 10h; Inert atmosphere; Schlenk technique; Irradiation; | General experimental procedure for synthesis of 5a-q General procedure: An 25 mL oven-dried Schlenk tube was equipped with a stirring bar, an aziridine 1 (0.5 mmol), PhN2BF4 (0.6 mmol, 1.2 eq), and Ru(bpy)3(BF4)2 (0.005 mmol, 1 mol%). The mixture was degassed by using standard Schlenk techniques with the oil pump. Then isothiocyanate 4 (1.5 mmol, 3 eq), and DCE (3 mL) were injected into the reaction tube. The reaction mixture was allowed to stir for 10 h under irradiation of 45 W CFL (FSL, YPZ220/45-S, Luminous Flux (2580Lm) at rt, the distance from the light bulb to the reaction vessel being about 5 cm. After the reaction was complete (TLC), the tot he mixture was added distilled water (10 mL) and product extracted with CH2Cl2 (3 × 30 ml) in separatory funnel. The combined the organic layers were dried (Na2SO4), the organic solution was concentrated under reduced pressure using a rotary evaporator and the residue purified by column chromatography on silica gel (200-300 mesh) (PE:EtOAc = 5-10:1) to give the pure product 5.N,5-Diphenyl-3-tosylthiazolidin-2-imine (5a). White solid, mp 129-131 °C (lit. 132-133 °C)32; 1H NMR (500 MHz, CDCl3) δ 8.00 (d, J 8.4 Hz, 2H, Ph in Ts), 7.38-7.33 (m, 7H, Ph in Ts and 5-Ph), 7.28-7.26 (m, 2H, PhN=), 7.08 (t, J 7.4 Hz,1H, PhN=), 6.81-6.79 (m, 2H, PhN=), 4.82 (dd, J 8.6, 6.5 Hz, 1H, CH2), 4.62 (dd, J 10.4, 6.5 Hz, 1H, CH2), 4.07 (dd, J 10.4, 8.6 Hz, 1H, CHS), 2.50 (s, 3H, -Me). 13C NMR (125 MHz, CDCl3) δ 152.1, 150.1, 144.9, 136.5, 134.7, 129.24, 129.20, 129.05, 128.97, 128.8, 127.5, 124.3, 120.8, 56.8, 47.0, 21.7. MS (ESI): ([M+H]+) 409.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44.444 % de | Stage #1: ethyl 2-((4-chlorophenyl)amino)acetate; N-(p-tolylsulfonyl)-2-phenylaziridine With copper(II) bis(trifluoromethanesulfonate) In toluene at 100℃; for 1h; Stage #2: With oxygen; trifluoroacetic acid In toluene at 100℃; for 3h; Overall yield = 60 %; Overall yield = 145 mg; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With nickel(II) bromide dimethoxyethane; [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; C24H34N2O6S2 In 1,4-dioxane at 20℃; for 48h; Inert atmosphere; Irradiation; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With manganese; (1,2-dimethoxyethane)dichloronickel(II); (4R,4'R)-4,4'-di(heptan-4-yl)-4,4',5,5'-tetrahydro-2,2'-bioxazole; sodium iodide In tetrahydrofuran at -10℃; for 72h; Sealed tube; Inert atmosphere; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: N-(p-tolylsulfonyl)-2-phenylaziridine; 2-bromo-6-nitro-phenol With lithium perchlorate In acetonitrile at 85℃; for 3h; Inert atmosphere; Stage #2: With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 10h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With lithium hydroxide; In acetonitrile; at 80.0℃; for 24.0h; | 0.25 mmol of aziridine of the formula 1a is added to the test tube.2a 0.15mmol, 70mol% LiOH, acetonitrile 0.8mL,The mixture was stirred at 80 C for 24 h, extracted, washed and dried to obtain a crude product;The crude product is purified by silica gel chromatography to obtain a ring-shaped product in a single configuration.The structural formula is as shown in 3a in Table 1, using nuclear magnetic resonance spectroscopy,Characterization of the product by carbon spectrum and high resolution mass spectrometry confirmed the structure of the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With perchloric acid; In neat (no solvent); at 20℃; for 0.0833333h;Milling; | General procedure: A mixtureof aziridine 1 (0.25 mmol), nitrile 2 or 4 (0.25 mmol) and perchloric acid(0.25 mmol) was placed in a mortar. The reaction mixture was thoroughlyground at room temperature for 5 min. After completion (TLC) the reactionmixture was diluted with a 1 : 1 water/ethyl acetate mixture (10 ml) andwashed with sodium bicarbonate (10 ml) followed by brine solution (10 ml).Then the combined organic layer was dried over anhydrous Na2SO4.Evaporation of solvent furnished the crude product which was subjectedto column chromatography using ethyl acetate-light petroleum as eluentto obtain the analytically pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Stage #1: 6-fluoroindoline; N-(p-tolylsulfonyl)-2-phenylaziridine at 20℃; for 4h; Stage #2: With sodium hypochlorite; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane; water at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With tetrakis(actonitrile)copper(I) hexafluorophosphate; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; 2-(2,4,6-tribromophenyl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-4-ium tetrafluoroborate; caesium carbonate; 2,6-bis(4,5-dihydrooxazol-2-yl)pyridine In dimethyl sulfoxide at 35℃; for 10h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With tetrakis(actonitrile)copper(I) hexafluorophosphate; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; 2-(2,4,6-tribromophenyl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-4-ium tetrafluoroborate; caesium carbonate; 2,6-bis(4,5-dihydrooxazol-2-yl)pyridine In dimethyl sulfoxide at 35℃; for 10h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction; |
Tags: 24395-14-0 synthesis path| 24395-14-0 SDS| 24395-14-0 COA| 24395-14-0 purity| 24395-14-0 application| 24395-14-0 NMR| 24395-14-0 COA| 24395-14-0 structure
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
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 |
Sorry,this product has been discontinued.
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