Reaktion #64844

Reaktionsgleichung

4-Acryloyl-2,3,4,5-tetrahydro-1,4-benzothiazepine

sulfuryl chloride

water

→

4-acryloyl-2-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine

Ausbeute 90.7%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with chloroform
2. 2
   WaschenThe chloroform phase was washed with a saturated saline solution
3. 3
   Sonstigedried on sodium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled out under reduced pressure
5. 5
   SonstigeResidue was purified by silica gel column chromatography (Wako Gel C-200, 200 g)
6. 6
   Wascheneluted with a mixed solvent of n-hexane (70 parts)+ethyl acetate (30 parts)

Vorschrift

4-Acryloyl-2,3,4,5-tetrahydro-1,4-benzothiazepine (10 g) was dissolved in methylene chloride (150 ml) and sulfuryl chloride (9.3 g) was added thereto under ice cooling and agitated at 0° C. for 1 hour. To the reaction mixture water was added and extracted with chloroform. The chloroform phase was washed with a saturated saline solution and dried on sodium sulfate and thereafter the solvent was distilled out under reduced pressure. Residue was purified by silica gel column chromatography (Wako Gel C-200, 200 g) and eluted with a mixed solvent of n-hexane (70 parts)+ethyl acetate (30 parts) to give 4-acryloyl-2-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine (10.5 g).

Quelle