Dimethylformamide → 2-Tert-butyl-5-dimethylamino-4-formyl-3(2H)-pyridazinone

HRID 1291221Notes

Reaction equation

HRID 1291221 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([N:10]1[C:15](=[O:16])[CH:14]=[C:13]([N:17]([CH3:19])[CH3:18])[CH:12]=[N:11]1)([CH3:9])([CH3:8])[CH3:7].CN([CH:23]=[O:24])C>>[C:6]([N:10]1[C:15](=[O:16])[C:14]([CH:23]=[O:24])=[C:13]([N:17]([CH3:19])[CH3:18])[CH:12]=[N:11]1)([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 189189072-t-butyl-5-dimethylamino-3(2H)-pyridazinone

Product 1

HCID 189188952-Tert-butyl-5-dimethylamino-4-formyl-3(2H)-pyridazinone

Procedure

Phosphorus oxychloride (6.5 g) was added dropwise to DMF (15 ml) with ice-cooling and the mixture was stirred at room temperature for 30 minutes. Then, 2-t-butyl-5-dimethylamino-3(2H)-pyridazinone (3.3 g)/DMF (40 ml) was added dropwise with ice-cooling and the mixture was stirred at 70° C. for 1 hour. This reaction mixture was poured gradually into ice-NaHCO3 /water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated to dryness. The residue was washed with n-hexane and dried. Yellow powder, 3.7 g. 1H-NMR (CDCl3) δ: 1.63(9H,s), 3.10(6H,s), 7.71(1H,s), 10.27(1H,s).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at 70° C. for 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous NaCl solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated to dryness
  8. washThe residue was washed with n-hexane
  9. customdried

Sources & evidence

ORD record
ord-075a95243aea44b8bcc85fbe53ce03b1
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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