Reaktion #602325

Reaktionsgleichung

3-fluorobenzyl bromide

2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide

sodium hydroxide

→

2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-6-methyl-4-morpholin-4-yl-benzamide

Ausbeute 16.0%

Lösungsmittel

benzene

water

benzene tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter completion of the reaction (monitored by TLC)
2. 2
   Extraktionextracted with ethyl acetate (15×3 ml)
3. 3
   WaschenThe organic layer is washed with water (20 ml), brine (15 ml)
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Sonstigeevaporated
6. 6
   Sonstigeto get the crude product, which
7. 7
   Sonstigeis purified by column chromatography (silica gel, 25% ethyl acetate/hexane)

Vorschrift

To a solution of 2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide (0.26 g, 0.92 mmol) in benzene-tetrahydrofuran (1:1) (20 ml) are added tetrabutylammonium hydrogensulfate (0.031 g, 0.091 mmol) and 50% sodium hydroxide solution (8 ml) at RT. The reaction mixture is heated to 80° C. and 3-fluorobenzyl bromide (0.14 ml of a 2M solution in benzene, 0.28 mmol) is added. The reaction mixture is stirred at 80° C. for 15 min. After completion of the reaction (monitored by TLC), the reaction mixture is diluted with water (15 ml) and extracted with ethyl acetate (15×3 ml). The organic layer is washed with water (20 ml), brine (15 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 25% ethyl acetate/hexane) to yield 2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-6-methyl-4-morpholin-4-yl-benzamide (example 1) (0.06 g, 0.15 mmol, 16%). [M+H]+ 389.1.

Quelle