Acetyl chloride → N-(3',4'-dichlorophenyl)-3,4-dimethyl-2-acetoxy-5-oxo-2,5-dihydropyrrole

HRID 27186Notes

Reaction equation

HRID 27186 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]2[OH:17])[CH:5]=[CH:6][C:7]=1[Cl:8].C([O-])([O-])=O.[K+].[K+].[C:24](Cl)(=[O:26])[CH3:25]>C(C(C)=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:10](=[O:17])[C:11]([CH3:16])=[C:12]([CH3:15])[CH:13]2[O:14][C:24](=[O:26])[CH3:25])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 13069714N-(3',4'-Dichlorophenyl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole

Product 1

HCID 13069715N-(3',4'-dichlorophenyl)-3,4-dimethyl-2-acetoxy-5-oxo-2,5-dihydropyrrole

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

27.2 g of N-(3',4'-dichlorophenyl-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole (see Example 3) is refluxed together with 20.7 g of K2CO3 in 150 ml of methyl ethyl ketone. After cooling, there is added dropwise 8.2 g of acetyl chloride, with the temperature of the reaction mixture rising from 15° to 35°. The reaction mixture is filtered after 24 hours, and the filtrate is concentrated by evaporation. The residue is recrystallised from methanol to give 23.9 g (76% of theory) of the above product in the form of colourless crystals, m.p. 109°-110°.

Workup

  1. temperatureAfter cooling
  2. customrising from 15° to 35°
  3. filtrationThe reaction mixture is filtered after 24 hours
  4. concentrationthe filtrate is concentrated by evaporation
  5. customThe residue is recrystallised from methanol
  6. customto give 23.9 g (76% of theory) of the above product in the form of colourless crystals, m.p. 109°-110°

Sources & evidence

ORD record
ord-452dc41dcc754181b5054dc81acc403b
Source dataset
uspto-grants-1980_09
Patent number
US04220655

Reaction notes

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