Carbon Disulfide → (RS)-9,9a-dihydrothiazolo[3,4-a]indole-3-thione

HRID 262121Notes

Reaction equation

HRID 262121 reaction equation
[C:1](=[S:3])=[S:2].OS(O[CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11]1)(=O)=O>[OH-].[Na+]>[CH2:9]1[CH:10]2[CH2:18][C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]2[C:1](=[S:3])[S:2]1

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 21320152(RS)-2-hydroxysulphonyloxymethylindoline

Product 1

HCID 21320146(RS)-9,9a-dihydrothiazolo[3,4-a]indole-3-thione

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

Carbon disulphide (65 cc) is added to a suspension of (RS)-2-hydroxysulphonyloxymethylindoline (45.8 g) in 1.5 N aqueous sodium hydroxide solution (400 cc). After stirring for 2 hours at a temperature of about 20° C., a solution is obtained and the formation of beige crystals is then observed; stirring is continued for 12 hours. The crystals formed are filtered off, washed with water and then recrystallised from ethanol (850 cc). (RS)-9,9a-dihydrothiazolo[3,4-a]indole-3-thione (31.3 g) is thus obtained in the form of white crystals melting at 132° C.

Workup

  1. customa solution is obtained
  2. stirringstirring
  3. waitis continued for 12 hours
  4. customThe crystals formed
  5. filtrationare filtered off
  6. washwashed with water
  7. customrecrystallised from ethanol (850 cc)

Sources & evidence

ORD record
ord-1fd7ba3f4027423f97d94b5e29a5d35e
Source dataset
uspto-grants-1979_05
Patent number
US04153699

Reaction notes

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