Ethanol → HCID 19081390, compound

HRID 963192Notes

Reaction equation

HRID 963192 reaction equation
C(O)C.[C:4]([N:8]1[C:13](=[O:14])[C:12]([CH:15]([F:17])[F:16])=[C:11](Cl)[CH:10]=[N:9]1)([CH3:7])([CH3:6])[CH3:5].[N:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH2:26])=[CH:21][CH:20]=1>C(N(CC)CC)C>[C:4]([N:8]1[C:13](=[O:14])[C:12]([CH:15]([F:17])[F:16])=[C:11]([NH:26][CH2:25][C:22]2[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=2)[CH:10]=[N:9]1)([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 773174-PyridinemethanamineHCID 19081385HCID 19081385, compound

Product 1

HCID 19081390HCID 19081390, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

20 ml of an absolute ethanol solution of 0.71 g of 2-tert-butyl-5-chloro-4-difluoromethylpyridazin-3-(2H)-one, 0.33 g of 4-picolylamine and 0.33 g of triethylamine, was reacted for 5 hours under heating and refluxing and left to cool. Then, the mixture was extracted with ethyl acetate, then washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off. The residue was subjected to column chromatography, and using an eluent (n-hexane:ethyl acetate=1:2), 0.32 g of the desired product (Compound No. 12) having a melting point of from 142° to 143° C. and 0.04 g of amorphous 2-tert-butyl-5-(4-pyridylmethylamino)-4-(4-pyridylmethyliminomethylidenyl)pyridazin-3-(2H)-one (Compound No. 2) as a by-product, were obtained.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. waitleft
  4. temperatureto cool
  5. extractionThen, the mixture was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customof from 142° to 143° C. and 0.04 g of amorphous 2-tert-butyl-5-(4-pyridylmethylamino)-4-(4-pyridylmethyliminomethylidenyl)pyridazin-3-(2H)-one (Compound No. 2)
  10. customwere obtained

Sources & evidence

ORD record
ord-302f035afa5a4448974c09394fafb8ec
Source dataset
uspto-grants-1998_06
Patent number
US05763439

Reaction notes

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