Carbon Disulfide → 6-methyloxazolo[4,5-b]pyridine-2(3H)-thione

HRID 70145Notes

Reaction equation

HRID 70145 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH-:10].[K+].[C:12](=[S:14])=S>C(O)CO.[Cu]>[CH3:8][C:6]1[CH:7]=[C:2]2[O:10][C:12](=[S:14])[NH:9][C:3]2=[N:4][CH:5]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 5193802-Amino-3-bromo-5-methylpyridine

Product 1

HCID 596716056-methyloxazolo[4,5-b]pyridine-2(3H)-thioneYield 93%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 174Ethylene GlycolSolvent

Procedure

3-Bromo-2-amino-5-methylpyridine (1.0 g, 5.3 mmol), potassium hydroxide (1.19 g, 21.2 mmol) and copper powder (17 mg, 0.27 mmol) were heated to 150° C. in ethylene glycol (2.3 mL). After 4 h, the reaction mixture was allowed to cool to rt, carbon disulfide (10 mL) was added, and heating was continued at 70° C. overnight. Upon cooling to rt, the reaction mixture concentrated under reduced pressure. 1 N HCl (20 mL) was added, and the resulting dark solid was collected by filtration. The solid was washed with water (2×) and air dried followed by drying in a 35° C. vacuum oven, yielding 0.817 g (93%) of the title compound. LC-MS: RT=4.14 min, [M+H]+=167.0, ˜80% pure.

Workup

  1. temperatureheating
  2. waitwas continued at 70° C. overnight
  3. temperatureUpon cooling to rt
  4. concentrationthe reaction mixture concentrated under reduced pressure
  5. addition1 N HCl (20 mL) was added
  6. filtrationthe resulting dark solid was collected by filtration
  7. washThe solid was washed with water (2×) and air
  8. customdried
  9. customby drying in a 35° C. vacuum oven

Sources & evidence

ORD record
ord-6547cda206e44fb481382b23b0a36d34
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

Loading…