Hydrochloric Acid → HCID 54272299, compound

HRID 461816Notes

Reaction equation

HRID 461816 reaction equation
[C:1](=[S:3])=[S:2].OS(O[CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][NH:11]1)(=O)=O.Cl>[OH-].[Na+]>[CH2:9]1[C@@H:10]2[N:11]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[CH2:19]2)[C:1](=[S:3])[S:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 54239901HCID 54239901, compound

Product 1

HCID 54272299HCID 54272299, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Carbon disulphide (14 g.) is added dropwise, with vigorous stirring, to a solution of (R)-3-hydroxysulphonyloxymethyl-1,2,3,4-tetrahydroisoquinoline (33.9 g.) in 0.6N sodium hydroxide solution (1,000 cc.). After one hour at a temperature of about 20° C., a precipitate appears; stirring is continued for 15 hours. The mixture is neutralised by adding 4N hydrochloric acid. The crystals formed are filtered off and washed with water and then with ethanol. (R)-1,5,10,10a-Tetrahydrothiazolo[3,4-b]isoquinoline-3-thione (30.0 g.) is thus obtained in the form of white crystals melting at 150° C.

Workup

  1. waitis continued for 15 hours
  2. customThe crystals formed
  3. filtrationare filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-e828078bc05841c4ba909cd9dab44743
Source dataset
uspto-grants-1977_12
Patent number
US04064247

Reaction notes

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