Phenyl Isothiocyanate → 3-Phenyl-5-{[(prop-2-en-1-yl)sulfanyl]methyl}-2-sulfanylideneimidazolidin-4-one

HRID 846638Notes

Reaction equation

[CH2:1]([S:4][CH2:5][C@@H:6]([C:8]([OH:10])=O)[NH2:7])[CH:2]=[CH2:3].[OH-].[Na+].[C:13]1([N:19]=[C:20]=[S:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:13]1([N:19]2[C:8](=[O:10])[CH:6]([CH2:5][S:4][CH2:1][CH:2]=[CH2:3])[NH:7][C:20]2=[S:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Reactant 3

HCID 7673Phenyl Isothiocyanate

HCID 14798Sodium Hydroxide

HCID 9793905S-Allylcysteine

Product 1

HCID 152957463-Phenyl-5-{[(prop-2-en-1-yl)sulfanyl]methyl}-2-sulfanylideneimidazolidin-4-one

Procedure

When 5 g of S-allylcysteine (0.031 mole), 1.24 g of sodium hydroxide (0.31 mole) and 4.19 g of phenylisothiocyanate (0.031 mole) were reacted according to the procedure for the preparation of the compound of Example 2, 8.59 g of crude product was obtained which did not require purification by chromatography. Crystallization of the crude product from isopropyl alcohol gave pure title compound: RF on silica gel=0.44 [ethyl acetate-hexane (2:3)].

Workup

custom8.59 g of crude product was obtained which
custompurification by chromatography
customCrystallization of the crude product from isopropyl alcohol

Sources & evidence

ORD record: ord-aaaf8f05363e45a3b373867a1259fdd2
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05137904

Reaction notes

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