Methyl chloroformate → 6-(3,5-Dichloro-4-methylphenyl)-2-methoxycarbonyl-3-pyridazone

HRID 1277939Notes

Reaction equation

HRID 1277939 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][CH3:21])=[O:19]>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[N:14]([C:18]([O:20][CH3:21])=[O:19])[N:15]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 93341Diclomezine

Product 1

HCID 128816346-(3,5-Dichloro-4-methylphenyl)-2-methoxycarbonyl-3-pyridazoneYield 94%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2.55 g of 6-(3,5-dichloro-4-methylphenyl)-3-pyridazone, 4.7 g of methyl chloroformate and 25 ml of xylene was heated under reflux for 1.5 hours. The reaction mixture was then left to cool at room temperature and the precipitate thus produced was collected by filtration and washed with hexane, giving 2.94 g (94%) of the desired Compound No. 23 in the form of colourless prisms having, after recrystallization from benzene, a melting point of 203°-206° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. waitThe reaction mixture was then left
  4. customthe precipitate thus produced
  5. filtrationwas collected by filtration
  6. washwashed with hexane

Sources & evidence

ORD record
ord-b58d09bf7b4945368d789b54a0a9180e
Source dataset
uspto-grants-1981_07
Patent number
US04279908

Reaction notes

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