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

HRID 2257771Notes

Reaction equation

HRID 2257771 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: mp 187°-189° C.; MS (FD) m/e 282 (M+).

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-9ca3f4013afe4280bf3c3976c41ef8da
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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