Carbon Disulfide → (10aS)-1,5,10,10a-Tetrahydro-3H-[1,3]thiazolo[3,4-b]isoquinoline-3-thione

HRID 461807Notes

Reaction equation

HRID 461807 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>[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

4

Reactant 2

HCID 6348Carbon DisulfideHCID 54239900(S)-3-hydroxysulphonyloxymethyl1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 54272298(10aS)-1,5,10,10a-Tetrahydro-3H-[1,3]thiazolo[3,4-b]isoquinoline-3-thioneYield 84.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Carbon disulphide (40 g.) is added dropwise at 20° C., with vigorous stirring, to a solution of (S)-3-hydroxysulphonyloxymethyl-1,2,3,4-tetrahydroisoquinoline (100 g) in 0.25N sodium hydroxide solution (4,000 cc.). The reaction is exothermic. A solid precipitates and the reaction mixture then sets solid. Stirring is continued for 3 hours. The reaction mixture is neutralised by adding 4N hydrochloride acid. The crystals formed are filtered off, washed copiously with water and then recrystallised from ethanol (3,000 cc.) to give (S)-1,5,10,10a-tetrahydrothiazolo[3,4-b]-isoquinoline-3-thione (77 g. ) in the form of fine white needles melting at 150° C.

Workup

  1. customA solid precipitates
  2. additionby adding 4N hydrochloride acid
  3. customThe crystals formed
  4. filtrationare filtered off
  5. washwashed copiously with water
  6. customrecrystallised from ethanol (3,000 cc.)

Sources & evidence

ORD record
ord-557bfc469eee41c7a30337231207ac01
Source dataset
uspto-grants-1977_12
Patent number
US04064247

Reaction notes

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