反応 #46337
ord-c2314251d3b343369891a1a11bae5b30
反応方程式
反応物
試薬
反応条件
後処理
- 1その他the solution obtained
- 2その他to return to room temperature
- 3温度is cooled to −20° C
- 4温度is maintained
- 5workup.STIRRINGAfter stirring for 2 hours at −20° C.
- 6workup.WAITfor 48 hours at 20° C.
- 7ろ過the mixture is filtered
- 8洗浄washed with three times 50 cm3 of diisopropyl ether
- 9その他dried under reduced pressure (2.7 kPa)
- 10その他A solid A is obtained
- 11濃縮The filtrate is concentrated to half the volume
- 12ろ過the resulting suspension is filtered
- 13洗浄washed with diisopropyl ether
- 14その他dried
- 15その他A solid B is obtained
- 16温度the mixture, cooled to 0° C.
- 17温度heated
- 18温度at reflux temperature for 3 hours
- 19温度The reaction mixture, cooled to +5° C.
- 20workup.STIRRINGstirred for 1 hour at room temperature
- 21温度The mixture is heated
- 22温度under reflux for one hour
- 23抽出The resulting mixture is extracted with 500 cm3 of ethyl acetate
- 24洗浄the organic phase is washed successively with a saturated aqueous sodium hydrogen carbonate solution
- 25乾燥with brine, and is then dried over magnesium sulfate
- 26濃縮concentrated to dryness under reduced pressure (2.7 kPa)
- 27その他the solution obtained
- 28洗浄is washed with 100 cm3 of ethyl acetate
- 29抽出is then extracted with twice 75 cm3 of ethyl acetate
- 30乾燥The combined extracts are dried over magnesium sulfate
- 31濃縮concentrated to dryness under reduced pressure (2.7 kPa)
実験手順
N-[3-(Methylsulfonylmethyl)phenyl]N-methylamine may be obtained by carrying out the procedure in the following manner: a mixture of 9.65 cm3 of formic acid and 19.63 cm3 of acetic anhydride is heated at 50° C. for 3 hours under argon, and then the solution obtained is allowed to return to room temperature. 40 cm3 of tetrahydrofuran are poured in and the medium is cooled to −20° C. After stirring for 2 hours at −20° C., a solution of 14.8 g of 3-(methylsulfonylmethyl)phenylamine is poured in while the temperature is maintained. After stirring for 2 hours at −20° C., and then for 48 hours at 20° C., the mixture is filtered, the solid is drained and then washed with three times 50 cm3 of diisopropyl ether and dried under reduced pressure (2.7 kPa). A solid A is obtained. The filtrate is concentrated to half the volume, the resulting suspension is filtered, the solid is drained, washed with diisopropyl ether and dried. A solid B is obtained. The two solids A and B are combined and taken up in 375 cm3 of tetrahydrofuran and the mixture, cooled to 0° C., is supplemented, over 20 minutes, with 80 cm3 of a 2 M solution of borane-dimethyl sulfide complex in tetrahydrofuran and then heated at reflux temperature for 3 hours. The reaction mixture, cooled to +5° C., is supplemented over 20 minutes with 60 cm3 of methanol, stirred for 1 hour at room temperature and then supplemented with gaseous hydrochloric acid to a pH of 1. The mixture is heated under reflux for one hour and then supplemented with 300 cm3 of water and with a 3 N solution of sodium hydroxide to pH 8. The resulting mixture is extracted with 500 cm3 of ethyl acetate, the organic phase is washed successively with a saturated aqueous sodium hydrogen carbonate solution, and with brine, and is then dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 100 cm3 of 4 N sulfuric acid, the solution obtained is washed with 100 cm3 of ethyl acetate, then alkalinized to pH 8 with 3 N sodium hydroxide and with a saturated aqueous sodium carbonate solution and is then extracted with twice 75 cm3 of ethyl acetate. The combined extracts are dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). 8.98 g of N-[3-(methylsulfonylmethyl)phenyl]N-methylamine are obtained in the form of a pink solid.