P-Anisidine → HCID 14881088, compound

HRID 2399230Notes

Reaction equation

HRID 2399230 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[CH3:7][O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.[O:16]1CCC[CH2:17]1>>[CH3:7][O:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:17]([N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 7732P-AnisidineHCID 8028TetrahydrofuranHCID 120252-Pyrrolidone

Product 1

HCID 14881088HCID 14881088, compoundYield 85%

Procedure

N,N'-Carbonyldiimidazole (3.85 g) and 2 g of 2-pyrrolidinone were added to 20 ml of tetrahydrofuran, and the mixture was refluxed with heating for 8 hours. Next, 2.9 g of 4-methoxyaniline was added to the reaction mixture, and the mixture was further refluxed with heating for 8 hours. The solvent was then distilled off, and the resulting residue was subjected to silica gel column chromatography to obtain a chloroform eluate and crystals from, the eluate. The crystal were recrystallized from methanol, giving 4.7 g of 1-(4-methoxyphenylcarbamoyl)-2-pyrrolidinone (yield 85%) having a melting point of 113° to 114° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 8 hours
  3. temperaturethe mixture was further refluxed
  4. temperaturewith heating for 8 hours
  5. distillationThe solvent was then distilled off
  6. customto obtain a chloroform eluate and crystals from, the eluate
  7. customThe crystal were recrystallized from methanol

Sources & evidence

ORD record
ord-a38ab26e943748cfa837e711770b1d0a
Source dataset
uspto-grants-1995_09
Patent number
US05447944

Reaction notes

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