Hydrochloric Acid → HCID 14881096, compound

HRID 484067Notes

Reaction equation

HRID 484067 reaction equation
C[Si](C)(C)[O:3][CH:4]1[CH2:8][NH:7][C:6](=[O:9])[CH2:5]1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.[O:20]1CCC[CH2:21]1>>[C:13]1([NH:12][C:21]([N:7]2[CH2:8][CH:4]([OH:3])[CH2:5][C:6]2=[O:9])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 8028TetrahydrofuranHCID 150784242-Pyrrolidinone, 4-[(trimethylsilyl)oxy]-

Product 1

HCID 14881096HCID 14881096, compoundYield 72%

Procedure

A 8.14 g quantity of 4-trimethylsilyloxy-2-pyrrolidone [Farmaco Edizione Scientifica, 36, 845-855 (1981)] was dissolved in 100 ml of tetrahydrofuran, 7.62 g of N,N'-carbonyldiimidazole was added to the solution, and the mixture was refluxed for 20 hours. With addition of 4.38 g of aniline, the mixture was further refluxed for 7 hours, then cooled and stirred at room temperature for 0.5 hour with addition of 150 ml of 1N hydrochloric acid. The solvent was distilled off in a vacuum, the residue was subjected to silica gel column chromatography to obtain crystals from an eluate of chloroform/methanol=30/1. The crystals were recrystallized from acetone-hexane, giving 7.44 g of 1-phenylcarbamoyl-4-hydroxy-2-pyrrolidinone (yield 72%) having a melting point of 104° to 104.5° C.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. temperaturethe mixture was further refluxed for 7 hours
  3. temperaturecooled
  4. distillationThe solvent was distilled off in a vacuum
  5. customto obtain crystals from an eluate of chloroform/methanol=30/1
  6. customThe crystals were recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-8d947a9abe8f48d484166d1ec5dbee26
Source dataset
uspto-grants-1993_07
Patent number
US05229402

Reaction notes

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