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

HRID 1487703

Reaction equation

HRID 1487703 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-871eaabfd49c43c689f266cf4b065d7b
Source dataset
uspto-grants-2016_08
Patent number
US09428522B2

Linked notes

Loading…