Dimethylamine → 2-t-butyl-4-chloro-5-dimethylamino-3(2H)-pyridazinone

HRID 1291219Notes

Reaction equation

HRID 1291219 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8](Cl)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][NH:15][CH3:16]>C(O)C.O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([N:15]([CH3:16])[CH3:14])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 27822252-Tert-butyl-4,5-dichloro-2,3-dihydropyridazin-3-one

Product 1

HCID 189188582-t-butyl-4-chloro-5-dimethylamino-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

In ethanol-water (2:1) (45 ml)was dissolved 2-t-butyl-4,5-dichloro-3(2H)-pyridazinone (4.4 g) followed by addition of 50% dimethylamine (7.2 g), and the mixture was stirred at room temperature for 15 hours. After removal of ethanol, the residue was extracted with diethyl ether and the organic layer was washed with saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated to dryness. This residue was washed with n-hexane and dried. White powder, 4.4 g. 1H-NMR (CDCl3) δ: 1.63(9H,s), 3.10(6H,s), 7.57(1H,s).

Workup

  1. customAfter removal of ethanol
  2. extractionthe residue was extracted with diethyl ether
  3. washthe organic layer was washed with saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness
  6. washThis residue was washed with n-hexane
  7. customdried

Sources & evidence

ORD record
ord-bd9b7dbfe91846e7a43003a5310b5e7e
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…