Hydrazine hydrate (1:1) → 6-(3,5-dichloro-4-methylphenyl)-4-methylthio-4,5-dihydro-3(2H)-pyridazinone

HRID 746271Notes

Reaction equation

HRID 746271 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=O)[CH2:11][CH:12]([S:16][CH3:17])[C:13](O)=[O:14])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].O.[NH2:20][NH2:21]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:11][CH:12]([S:16][CH3:17])[C:13](=[O:14])[NH:20][N:21]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 134203114-(3,5-Dichloro-4-methylphenyl)-2-methylthio-4-oxobutyric acid

Product 1

HCID 133677496-(3,5-dichloro-4-methylphenyl)-4-methylthio-4,5-dihydro-3(2H)-pyridazinoneYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.54 g (0.005 mole) of 4-(3,5-dichloro-4-methylphenyl)-2-methylthio-4-oxobutyric acid, prepared as described in step (c) above, were suspended in 5 ml of ethanol and then 0.25 g of hydrazine monohydrate was added, at room temperature, to the suspension, after which the mixture was stirred for 1 hour at room temperature. The mixture was then heated under reflux for 6 hours, after which it was cooled and the resulting crystals were collected by filtration and washed with a small amount of ethanol, to give 1.32 g (yield 87.1%) of the desired Compound No. 22, melting at 163°-165° C.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 6 hours
  3. temperatureafter which it was cooled
  4. filtrationthe resulting crystals were collected by filtration
  5. washwashed with a small amount of ethanol

Sources & evidence

ORD record
ord-8e7635406da14b5897953b4e375b0509
Source dataset
uspto-grants-1986_07
Patent number
US04603201

Reaction notes

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