Acetic Acid → 3-Methyl-1-(4-methoxyphenylcarbamoyl)-2-pyrrolidinone

HRID 484070Notes

Reaction equation

HRID 484070 reaction equation
[H-].[Na+].[CH3:3][CH:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1.C(O)(=O)C>O1CCCC1.O>[CH3:3][CH:4]1[CH2:8][CH2:7][N:6]([C:19](=[O:20])[NH:18][C:15]2[CH:14]=[CH:13][C:12]([O:11][CH3:10])=[CH:17][CH:16]=2)[C:5]1=[O:9]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 794431-Isocyanato-4-methoxybenzeneHCID 1028483-Methylpyrrolidin-2-one

Product 1

HCID 148810993-Methyl-1-(4-methoxyphenylcarbamoyl)-2-pyrrolidinoneYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

While 2 g of sodium hydride (60% oily) was being stirred in 50 ml of tetrahydrofuran, 5 g of 3-methyl-2-pyrrolidinone was added to the mixture, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was cooled to not higher than 0° C., and 7.5 g of 4-methoxyphenyl isocyanate was added dropwise to the mixture, followed by stirring at the same temperature for 5 hours. Acetic acid was then added to the reaction mixture for neutralization, water was thereafter added to the mixture, and the solvent was distilled off in a vacuum. Water was added to the residue, and the precipitate was filtered off, giving 8.2 g of 3-methyl-1-(4-methoxyphenylcarbamoyl)-2-pyrrolidinone (yield 66%) having a melting point of 71° to 72° C.

Workup

  1. temperatureThe reaction mixture was cooled to not higher than 0° C.
  2. stirringby stirring at the same temperature for 5 hours
  3. additionwas thereafter added to the mixture
  4. distillationthe solvent was distilled off in a vacuum
  5. additionWater was added to the residue
  6. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-f08f787b2cf7493baa7f6fe5b6f27cfd
Source dataset
uspto-grants-1993_07
Patent number
US05229402

Reaction notes

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