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

HRID 1577083
Notes
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Reaction equation

HRID 1577083 reaction equation
[CH2:1]1[C@H:13]2[N:4]([CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:12]2)[C:3](=[S:14])[S:2]1.[CH2:15]([I:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(OC(C)C)(C)C>C(Cl)Cl>[I-:22].[CH2:15]([S:14][C:3]1[S:2][CH2:1][C@@H:13]2[CH2:12][C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[CH2:5][N+:4]=12)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 12098Benzyl iodideHCID 54272298(10aS)-1,5,10,10a-Tetrahydro-3H-[1,3]thiazolo[3,4-b]isoquinoline-3-thione

Product 1

HCID 86737983(S)-3-Benzylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodideYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

(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.

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. washwashed with diisopropyl ether
  3. customdried at 20° C. under reduced pressure (1 mm Hg; 0.13 kPa)

Sources & evidence

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

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes