Phosphorus sulfide (P2S5) → 6-(3,5-Dichloro-4-methylphenyl)-3(2H)pyridazinethione

HRID 1277942Notes

Reaction equation

HRID 1277942 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13](=O)[NH:14][N:15]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:18]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13](=[S:18])[NH:14][N:15]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 93341Diclomezine

Product 1

HCID 129458916-(3,5-Dichloro-4-methylphenyl)-3(2H)pyridazinethioneYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

12.75 g of 6-(3,5-dichloro-4-methylphenyl)-3-pyridazone and 22 g of phosphorus pentasulphide in 80 ml of pyridine were heated under reflux on an oil bath for 7 hours. The reaction mixture was then cooled to room temperature and its volume was reduced by one-half by distilling off the pyridine under reduced pressure. 300 ml of ethyl acetate were added to the residue and the mixture was poured into ice-water. After stirring the mixture for a short time, the resulting yellow solid was collected by filtration, washed with water and dried to give 7.5 g (56%) of the desired compound. After recrystallizing the compound from a 10:1 by volume mixture of ethanol and dioxan, the compound melted at 255°-258° C.

Workup

  1. temperatureunder reflux on an oil bath for 7 hours
  2. distillationby distilling off the pyridine under reduced pressure
  3. addition300 ml of ethyl acetate were added to the residue
  4. additionthe mixture was poured into ice-water
  5. filtrationthe resulting yellow solid was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-2dc26b45efdb4f6d8321322acc64cfb9
Source dataset
uspto-grants-1981_07
Patent number
US04279908

Reaction notes

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