Thionyl Chloride → N-(3',4'-Dichlorophenyl)-3,4-dimethyl-2-chloro-5-oxo-2,5-dihydropyrrole

HRID 27187Notes

Reaction equation

HRID 27187 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]2O)[CH:5]=[CH:6][C:7]=1[Cl:8].S(Cl)([Cl:20])=O>>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]2[Cl:20])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 13069714N-(3',4'-Dichlorophenyl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole

Product 1

HCID 13069716N-(3',4'-Dichlorophenyl)-3,4-dimethyl-2-chloro-5-oxo-2,5-dihydropyrrole

Procedure

27.2 g of N-(3',4'-dichlorophenyl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole (see Example 3) is added to 25 ml of thionyl chloride, with an intense evolution of gas occurring. After being stirred for one hour at 50°, the mixture is concentrated by evaporation in vacuo. The solid residue is triturated with petroleum ether to obtain 27.4 g (95% of theory) of the above compound in the form of light-yellow crystals, m.p. 95°-96°.

Workup

  1. concentrationthe mixture is concentrated by evaporation in vacuo
  2. customThe solid residue is triturated with petroleum ether
  3. customto obtain 27.4 g (95% of theory) of the above compound in the form of light-yellow crystals, m.p. 95°-96°

Sources & evidence

ORD record
ord-911ca978e7994602922686e1b9d8dd0d
Source dataset
uspto-grants-1980_09
Patent number
US04220655

Reaction notes

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