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

HRID 2420097Notes

Reaction equation

HRID 2420097 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, with vigorous stirring, to a solution of (S)-3-hydroxysulphonyloxymethyl-1,2,3,4-tetrahydroisoquinoline (100 g) in 0.25N sodium hydroxide solution (4000 cc). The reaction is exothermic. A solid precipitates. Stirring is continued for a further 3 hours and then the reaction mixture is neutralised by the addition of 4N hydrochloric acid. The resulting crystals are filtered off, washed copiously with water and then recrystallised 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 melting at 150° C.

Workup

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

Sources & evidence

ORD record
ord-8ca2c67a758d421f8cf5ccd580309e1f
Source dataset
uspto-grants-1978_08
Patent number
US04108999

Reaction notes

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