| 51% |
With isopentyl nitrite; In acetonitrile; at 60℃; for 2h; |
To a suspension of 5-chloro-2- ( trifluorometnyl ) aniline (5.00 g, 23.6 mmol) and dibenzyl disulfide (4.66g, 18.9 mmol) in acetonitrile (75 mL) , Isoamyl nitrite (3.46 mL, 26.0 mmol) was slowly added at 60C in an oil bath, and the mixture was stirred at the same temperature as above for 2 hours. The reaction mixture was cooled and then concentrated under reduced pressure, and the residue was purified in an automatic chromatography apparatus (n-hexane/ethyl acetate = 100/0 - 95/5) to prepare 2- (benzylsulfanyl ) -4-chlorophenyl trifluoromethyl ether (3.86 g, yield: 51%) . To a mixture of the obtained 2- (benzylsulfanyl ) -4-chlorophenyl trifluoromethyl ether (4.84 g, 15.2 mmol), acetic acid(4.5 mL) and water (3 mL) in acetonitrile (120 mL) , 1, 3-dichloro-5, 5-dimethylhydantoin (5.98 g, 30.4 mmol) was added under ice cooling, and the mixture was stirred at the same temperature as above for 3 hours. The mixture was diluted by addition of a saturated aqueous solution of sodium bicarbonate, extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified in an automatic chromatography apparatus(hexane/ethyl acetate = 100/0 - 85/15) to obtain the title compound (3.64 g, yield: 81%) . NMR spectrum (CDC13, 400MHz) delta: 8.09 (1H, d, J =2.3 Hz), 7.75 (1H, dd, J = 9.0, 2.7 Hz), 7.50-7.47 (1H, m) . |
| 51% |
With isopentyl nitrite; In acetonitrile; at 20 - 60℃; for 2h; |
To a suspension of 5-chloro-2- (trifluoromethoxy)aniline (5.00 g, 23.6 mmol) and dibenzyl disulfide (4.66g, 18.9 mmol) in acetonitrile (75 mL), isoamyl nitrite (3.46 mL, 26.0 mmol) was slowly added at 60C in an oil bath, and the mixture was stirred at the same temperature as above for 2 hours. The reaction mixture was cooled and then concentrated under reduced pressure, and the residue was purified in an automatic chromatography apparatus (n-hexane/ethyl acetate = 100/0 - 95/5) to prepare 2-(benzylsulfanyl)-4- chlorophenyl trifluoromethyl ether (3.86 g, yield: 51%) To a mixture of 2-(benzylsulfanyl)-4-chlorophenyl trifluoromethyl ether (4.84 g, 15.2 mmol) obtained in the above step, acetic acid (4.5 mL) and water (3 mL) in acetonitrile (l2OmL), 1,3-dichloro-5,5-dimethylhydantoin (5.98 g, 30.4 mmol) was added under ice cooling, and the mixture was stirred at the same temperature as above for 3 hours. The mixture was diluted by addition of a saturated aqueous solution of sodium bicarbonate, extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified in an automatic chromatography apparatus (hexane/ethyl acetate = 100/0 - 85/15) to obtain the title compound (3.64 g, yield: 81%) ?H NNR spectrum (CDC13, 400MHz) oe: 8.09 (1H, d, J =2.3 Hz), 7.75 (1H, dd, J = 9.0, 2.7 Hz), 7.50-7.47 (1H, m) |
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
