Carbon Disulfide → [1,3]Thiazolo[5,4-b]pyridine-2(1H)-thione

HRID 344711Notes

Reaction equation

HRID 344711 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:9](=[S:11])=[S:10]>CN(C=O)C>[NH:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[N:4][C:3]=2[S:11][C:9]1=[S:10]

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 2782239[1,3]Thiazolo[5,4-b]pyridine-2(1H)-thioneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.43 g (50.0 mmols) of 3-amino-2-chloropyridine, 50 ml of carbon disulfide and 50 ml of DMF was heated under reflux for 6 days. An excess of carbon disulfide was evaporated under reduced pressure, and the residue was poured into 300 ml of ice water with stirring. The precipitated crystals was taken out by filtration and dried to afford 7.57 g (yield: 90%) of pyrido[3,2-d]thiazo-line-2-thione.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 days
  3. customAn excess of carbon disulfide was evaporated under reduced pressure
  4. additionthe residue was poured into 300 ml of ice water
  5. filtrationThe precipitated crystals was taken out by filtration
  6. customdried

Sources & evidence

ORD record
ord-8942ed11f1d2461db98673c7d5d75d84
Source dataset
uspto-grants-1991_10
Patent number
US05053408

Reaction notes

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