Carbon Disulfide → (1,3)Oxazolo(4,5-b)pyridine-2-thiol

HRID 70127

Reaction equation

HRID 70127 reaction equation
[OH:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[C:11](=S)=[S:12]>CCO>[O:1]1[C:2]2[C:3](=[N:4][CH:5]=[CH:6][CH:7]=2)[NH:8][C:11]1=[S:12]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 658727(1,3)Oxazolo(4,5-b)pyridine-2-thiolYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Hydroxy-2-aminopyridine (2.00 g, 18.2 mmol) and potassium hydroxide (1.22 g, 21.8 mmol) were dissolved in carbon disulfide (15 mL) and EtOH (25 mL), and the reaction mixture was heated to reflux overnight. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure. The resulting solid was suspended in 1 M aqueous HCl, collected by filtration, washed with water (2×) and air-dried. Further drying in a 35° C. vacuum oven gave 2.52 g (91%) of the title compound as a tan solid. LC-MS: RT=4.82 min., [M+H]+=153.1

Workup

  1. temperatureto reflux overnight
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. filtrationcollected by filtration
  4. washwashed with water (2×)
  5. customair-dried
  6. customFurther drying in a 35° C. vacuum oven

Sources & evidence

ORD record
ord-19e6337ddada4661bb84eebb88a950a1
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Linked notes

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