Benzyl Isothiocyanate → 3-Benzyl-5-(benzylsulfanylmethyl)-2-sulfanylideneimidazolidin-4-one

HRID 846639

Reaktionsgleichung

Reaktionsgleichung von HRID 846639
[CH2:1]([S:8][CH2:9][C@@H:10]([C:12]([OH:14])=O)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:17]([N:24]=[C:25]=[S:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)(C)C>[C:18]1([CH2:17][N:24]2[C:12](=[O:14])[CH:10]([CH2:9][S:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[NH:11][C:25]2=[S:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 2346Benzyl IsothiocyanateHCID 14798Sodium HydroxideHCID 193613S-benzyl-L-cysteine

Produkt 1

HCID 28718503-Benzyl-5-(benzylsulfanylmethyl)-2-sulfanylideneimidazolidin-4-oneAusbeute 8,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

When 2 g of S-benzylcysteine (0.0095 mole), 0.41 g of sodium hydroxide (0.0104 mole) and 1.55 g of benzylisothiocyanate (0.0104 mole) was treated according to the procedure for the preparation of the compound of Example 2, 0.289 g of pure title compound was obtained by crystallization from isopropyl alcohol: 1H NNR was consistent with the assigned structure for the thiohydantoin.

Quellen und Nachweise

ORD-Eintrag
ord-63aae8b1d4c649868a8bd5cc9354ef2e
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05137904

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