Potassium Carbonate → 2-Butoxycarbonyl-6-(3,5-dichloro-4-methylphenyl)-3-pyridazone

HRID 1277941Notes

Reaction equation

HRID 1277941 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][N:15]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].Cl[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:21]([O:20][C:18]([N:14]1[C:13](=[O:16])[CH:12]=[CH:11][C:10]([C:4]2[CH:5]=[C:6]([Cl:9])[C:7]([CH3:8])=[C:2]([Cl:1])[CH:3]=2)=[N:15]1)=[O:19])[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 61140Butyl chloroformateHCID 93341Diclomezine

Product 1

HCID 128816372-Butoxycarbonyl-6-(3,5-dichloro-4-methylphenyl)-3-pyridazoneYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.55 g of 6-(3,5-dichloro-4-methylphenyl)-3-pyridazone, 1.43 g of butyl chloroformate, 1.75 g of potassium carbonate and 100 ml of acetonitrile was heated under reflux for 7.5 hours. After cooling the reaction mixture, the unreacted pyridazone and inorganic salts were removed by filtration and the solvent was distilled under reduced pressure from the filtrate. The residue was recrystallized from hexane, giving 1.1 g (31%) of the desired Compound No. 32, in the form of needles, whose melting point and spectroscopic data agreed completely with those of the compound obtained in Example 6.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7.5 hours
  3. temperatureAfter cooling the reaction mixture
  4. customthe unreacted pyridazone and inorganic salts were removed by filtration
  5. distillationthe solvent was distilled under reduced pressure from the filtrate
  6. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-5b45556688954b6c8feb1c5ce4d57e5f
Source dataset
uspto-grants-1981_07
Patent number
US04279908

Reaction notes

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