Dimethylformamide → HCID 54373171, compound

HRID 1981511Notes

Reaction equation

HRID 1981511 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1C1C=CC(=O)NC=1.[CH3:16][C:17]1C=CC(S(C)(=O)=O)=C[CH:22]=1.[CH3:27][N:28]([CH:30]=[O:31])[CH3:29]>>[CH3:27][N:28]1[CH:29]=[C:22]([N:3]2[CH:4]=[CH:5][N:6]=[CH:7][CH2:8]2)[CH:17]=[CH:16][C:30]1=[O:31]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 18521p-Tolyl methyl sulfoneHCID 24758Sodium hydrideHCID 233188115-(Pyrazin-2-yl)pyridin-2(1H)-one

Product 1

HCID 54373171HCID 54373171, compound

Procedure

Sodium hydride (0.75 g) is added to a stirred solution of 5-(2-pyrazinyl)-2(1H) pyridone (2.2 g) in DMF (150 ml). Methyl p-toluene sulfonate (4.0 g) is added to the stirred reaction mixture after 5 minutes of stirring. After 35 minutes reaction time at RT, the reaction mixture is filtered and the filtrate evaporated in vacuum. The oily solid residue is washed with ether, filtered and the dry solid treated with hot acetone. The acetone is filtered and the filtrate evaporated, yielding a solid. The ether filtrate from above is evaporated, yielding a solid which after washing with decane is combined with the acetone filtrate solid. The combined solids are recrystallized from toluene and decane (treated with charcoal and filtered while hot) resulting in the desired 1-methyl pyridone compound, M.P. 165.5°-166.5° C.

Workup

  1. customAfter 35 minutes reaction time at RT
  2. filtrationthe reaction mixture is filtered
  3. customthe filtrate evaporated in vacuum
  4. washThe oily solid residue is washed with ether
  5. filtrationfiltered
  6. additionthe dry solid treated with hot acetone
  7. filtrationThe acetone is filtered
  8. customthe filtrate evaporated
  9. customyielding a solid
  10. customThe ether filtrate from above is evaporated
  11. customyielding a solid which
  12. washafter washing with decane
  13. customThe combined solids are recrystallized from toluene and decane (treated with charcoal and filtered while hot)

Sources & evidence

ORD record
ord-eed850859f7a422893ebdc20948fa103
Source dataset
uspto-grants-1986_06
Patent number
US04593028

Reaction notes

Loading…