Acetyl chloride → HCID 19905725, compound

HRID 2372013Notes

Reaction equation

HRID 2372013 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([N:9]2[C:14](=[O:15])[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)=[C:12]([NH2:26])[CH:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[C:31](Cl)(=[O:33])[CH3:32].[O:35]1CCO[CH2:37][CH2:36]1>O>[F:28][C:2]([F:1])([F:27])[C:3]1[CH:4]=[C:5]([N:9]2[C:14](=[O:15])[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=3)=[C:12]([N:26]([C:36](=[O:35])[CH3:37])[C:31](=[O:33])[CH3:32])[CH:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 312751,4-Dioxane2×HCID 19905717HCID 19905717, compound

Product 1

HCID 19905725HCID 19905725, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4 g (0.01 mol) of 2,4-di-[3-trifluoromethylphenyl]-5-amino-2H-pyridazin-3-one in 50 ml of dioxane, 0.62 g (0.02 mol) of NaH (80% dispersion) is added and the mixture is warmed to 40° C. for 30 minutes. It is then cooled, 1.6 g (0.02 mol) of acetyl chloride dissolved in 30 ml of dioxane are added dropwise at 15°-20° C. and the mixture is then stirred at room temperature for 16 h. The reaction mixture is diluted with 300 ml of water and extracted twice with 150 ml of methylene chloride. The organic phase is washed with bicarbonate solution and water, dried over sodium sulphate and evaporated. The residue is chromatographed on silica gel 60 using methylene chloride and yields 2.3 g (47% of theory) of 2,4-di-[3-trifluoromethylphenyl]-5-diacetylamino-2H-pyridazin-3-one of melting point 174° C.

Workup

  1. temperatureIt is then cooled
  2. additionare added dropwise at 15°-20° C.
  3. extractionextracted twice with 150 ml of methylene chloride
  4. washThe organic phase is washed with bicarbonate solution and water
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customThe residue is chromatographed on silica gel 60 using methylene chloride

Sources & evidence

ORD record
ord-24bf800873af4a279a16ed43e6c7b0da
Source dataset
uspto-grants-1992_03
Patent number
US05097028

Reaction notes

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