Hydrochloric Acid → (RS)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline-3-thione

HRID 262111Notes

Reaction equation

HRID 262111 reaction equation
[C:1](=[S:3])=[S:2].OS(O[CH2:9][CH: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+].Cl>O>[CH2:9]1[CH: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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 21320142(RS)-3-hydroxysulphonyloxymethyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 20571807(RS)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline-3-thioneYield 77.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

Carbon disulphide (63 g) is added dropwise, at 20° C. and whilst stirring vigorously, to a solution of (RS)-3-hydroxysulphonyloxymethyl-1,2,3,4-tetrahydroisoquinoline (151 g) and sodium hydroxide pellets (63 g) in water (5000 cc). A cream precipitate is immediately formed. The very thick mixture is stirred at a temperature of about 20° C. for 24 hours. The reaction mixture is then neutralised by adding 4 N hydrochloric acid (130 cc). The solid is filtered off and then washed copiously with water. After drying, (RS)-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline-3-thione (107 g) is obtained in the form of white crystals which melt at 180° C.

Workup

  1. customA cream precipitate is immediately formed
  2. filtrationThe solid is filtered off
  3. washwashed copiously with water
  4. customAfter drying

Sources & evidence

ORD record
ord-52fda17093cd44c9921314100c77ec02
Source dataset
uspto-grants-1979_05
Patent number
US04153698

Reaction notes

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