Diisopropyl Ether → (S)-3-Benzylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropyl Ether	HCID 7914	—
Reactant	Benzyl iodide	HCID 12098	—
Reactant	(10aS)-1,5,10,10a-Tetrahydro-3H-[1,3]thiazolo[3,4-b]isoquinoline-3-thione	HCID 54272298	—
Solvent	Dichloromethane	HCID 6344	—
Product	(S)-3-Benzylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide	HCID 86737983	89.3%

Reaction Steps

(S)-1,5,10,10a-Tetrahydrothiazolo[3,4-b]-isoquinoline-3-thione (8.8 g) is dissolved in methylene chloride (100 cc), and benzyl iodide (9.5 g) is added. After 48 hours at a temperature of about 20° C., diisopropyl ether (200 cc) is added. The resulting precipitate is filtered off, washed with diisopropyl ether and dried at 20° C. under reduced pressure (1 mm Hg; 0.13 kPa). (S)-3-Benzylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (15.6 g) is thus obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04287197
Source dataset	uspto-grants-1981_09
ORD ID	ord-25d3c52c6f644e3e8a62f1cf7a987bc3
Source note	uspto-grants-1981_09