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To a solution of 1(5g) in THF(100mL) was added n-Butyllithium(3.19mL, 2.71M hexane solution) at -78 °C under N2 atmosphere, then the reaction solution was allowed warm up to -30 °C. After cooling again to -78 °C, diphenylsulfide(10.31g) in THF(40mL) was added to the reaction solution. After termination of this reaction, dilute hydrochloric acid was added to the solution. The solution was partitioned between water and Et2O, extracted with Et2O and washed with brine. The extraction was back extracted with sat.NaHCO3 soln. and the back extraction was washed with Et2O. It was neutralized with conc.HCl and the resulting precipitates were collected by filtration and washed with water to give 2 (6.41g).
With sodium dithionite; water; potassium carbonate; In dimethyl sulfoxide; at 60℃; for 0.75h;
General procedure: A mixture of isatoic anhydride 1 (0.6 mmol), disulfide 2 (0.2 mmol), and Na2S2O4 (0.9 mmol) in undried DMSO (2 mL) was stirred at 60 C for respective time in Table 2 and Scheme 2. After the completion of the reaction, as monitored by TLC and GC-MS analysis, the reaction mixture washed with brine and extracted with ethyl acetate. The organic phase was separated and dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and the resulting residue was purified by column chromatography on silica gel (300-400 mesh) with petroleum ether-EtOAc as eluent to provide the desired product.
With tert.-butylhydroperoxide; potassium carbonate; In water; at 100℃; for 2h;
General procedure: In a typical run, a mixture of diphenyl disulfide (0.2 mmol), p-tolualdehyde (2.0 mmol), K2CO3(0.4 mmol), tert-butyl hydroper-oxide (TBHP) (0.6 mmol), catalyst (40 mg), H2O (2.0 mL) was stirredat desired temperature for 2 h. After the reaction was completed,the mixture was cooled down to room temperature and thenextracted with ethyl acetate. The organic phase was analyzed on anAgilent 7890A GC equipped with a FID detector and mass spectrom-eter. The product was purified by column chromatography on silicagel (200?300 mesh) (eluent: petroleum ether and ethyl acetate).The obtained product was identified by NMR spectra using a Bruker500 MHz spectrometer instrument. The1H NMR (500 MHz) and13CNMR (125 MHz) were recorded with spectrometers at 20C usingCDCl3as the solvent. Chemical shifts are given in parts per millionrelative to TMS as the internal standard at room temperature. Thespectra data were consistent with authentic compounds.
5-bromo-2-methyl-3-(phenylthio)-1H-indole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
74%
With sodium iodide; In acetonitrile; at 20℃; for 18h;Irradiation;
General procedure: To a 20 mL glass tube with a stir bar was charged 2-methyl-1H-indole 1a (39.35 mg, 0.3 mmol), diphenyldisulfide 2a (65.50 mg, 0.3 mmol), NaI (0.06 mmol, 9 mg) and MeCN (2 mL). The solution was stirred at room temperature with the irradiation of a 12 W blue LED for 18 h. The solvent was removed under vacuum. The residue was purified by column chromatography over silica gel (petroleum ether/ethyl acetate = 15/1) to give the product 3a (60 mg, 83percent).
2,7-bis(phenylthio)-9,9′-spirobifluorene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With n-butyllithium; In tetrahydrofuran; for 0.5h;Cooling with ice;
A mixed solution of NBS (N-bromosuccinimide) / THF was added dropwise to a reaction flask equipped with 1 mol of A,In the nitrogen protection conditions heated to 40C for 1 hour, the bromination reaction to be B.then,JoinDibenzo-substituted disulfideDiphenyl disulfide compound Ph-S-S-Ph,The compound C was obtained by sufficiently stirring for half an hour with n-BuLi / THF as a catalyst in a low-temperature dry ice bath.Finally, a mixed solution of meta-chlorobenzoic acid mCPBA / CH2Cl2 was introduced, and the mixture was stirred for 1 hour,Add water, precipitate solid,Followed by recrystallization using n-hexane and ethanol to obtain SDF-DPSO2 in a yield of 38percent.
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