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

HRID 262109Notes

Reaction equation

HRID 262109 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, whilst stirring vigorously, to a solution of (S)-3-hydroxysulphonyloxymethyl-1,2,3,4-tetrahydroisoquinoline (100 g) in 0.25 N aqueous sodium hydroxide solution (4000 cc). The reaction is exothermic. A solid precipitates; the stirring is continued for 3 hours. The reaction mixture is then neutralised by the addition of 4 N hydrochloric acid. The resulting crystals are filtered off, washed copiously with water and then recrystallized from ethanol (3000 cc). (S)-1,5,10,10a-Tetrahydrothiazolo[3,4-b]isoquinoline-3-thione (77 g) is thus obtained in the form of fine white needles which melt at 150° C.

Workup

  1. customA solid precipitates
  2. additionThe reaction mixture is then neutralised by the addition of 4 N hydrochloric acid
  3. filtrationThe resulting crystals are filtered off
  4. washwashed copiously with water
  5. customrecrystallized from ethanol (3000 cc)

Sources & evidence

ORD record
ord-c7ceba0ceb71424faea771c246c26721
Source dataset
uspto-grants-1979_05
Patent number
US04153698

Reaction notes

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