Dl-Phenylalanine → 3-Phenyl-5-(phenylmethyl)-2-thioxo-4-imidazolidinone

HRID 861588Notes

Reaction equation

HRID 861588 reaction equation
[NH2:1][CH:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13]1([NH:19][C:20](=S)[S:21]C)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C(O)C>[CH2:3]([CH:2]1[NH:1][C:20](=[S:21])[N:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]1=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 994Dl-PhenylalanineHCID 8471TriethylamineHCID 3032344Carbamodithioic acid, phenyl-, methyl ester (9CI)

Product 1

HCID 28719113-Phenyl-5-(phenylmethyl)-2-thioxo-4-imidazolidinoneYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of DL-phenylalanine (1.65 g, 10 mmol), methyl N-phenyldithiocarbamate (1.85 g, 10 mmol), and triethylamine (1.4 mL, 10 mmol) in ethanol (30 mL) was heated at reflux for 5 h, the mixture was cooled to room temperature and the solvent removed in vacuo. The residue was dissolved in ethyl acetate, washed with 1N aqueous HCl and water. The organic layer was concentrated and the residue recrystallized form ethanol to provide 2.48 g (88%) of the titled product:

Workup

  1. temperatureat reflux for 5 h
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1N aqueous HCl and water
  5. concentrationThe organic layer was concentrated
  6. customthe residue recrystallized form ethanol

Sources & evidence

ORD record
ord-d34c859dbaaa45a889dd786637fdd16f
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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