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

HRID 861588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861588
[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

Komponenten

5

Edukt 3

HCID 994Dl-PhenylalanineHCID 8471TriethylamineHCID 3032344Methyl N-phenylcarbamodithioate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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:

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d34c859dbaaa45a889dd786637fdd16f
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05714503

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