1,2-Dichloroethane → HCID 12449425, compound

Participants

Reaction Steps

0.2 g of triethylbenzylammonium chloride, 3 g of trans-(+)-2-(4'-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepine-4(5H)-one and 6.4 g of barium octahydrate were added under vigorous stirring to 60 ml of 1,2-dichloroethane and 7 ml of water. A solution of 3.2 g of 2-(dimethylamino)-ethyl chloride-hydrochloride in 5 ml of water was added dropwise to the above mixture during 5 minutes. Stirring was continued at room temperature for 1 hour and then for 1.5 hours at 70°. After cooling to room temperature the aqueous phase was separated and discarded and the 1,2-dichloroethane was removed under vacuum. The residue was dissolved in 50 ml of toluene and then extracted with 50 ml of 3% HCl. The acidic extract was treated with an excess of a sodium bicarbonate solution and then extracted with 50 ml of toluene. The toluene was removed under vacuum to yield 3.5 g of trans (+)-2-(4' methoxyphenyl)-3-hydroxy-5-(2'-dimethylaminoethyl)-2,3-dihydro-1,5-benzothiazepine-4(5H)-one; m.p. 115°-117°.

Provenance & Evidence