Sodium Acetate → 2-Imino-5-[[4-(2-oxopropyl)phenyl]methyl]-1,3-thiazolidin-4-one

HRID 465439Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12](Cl)[C:13]([O:15]CC)=O)=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].[NH2:19][C:20]([NH2:22])=[S:21].C([O-])(=O)C.[Na+]>COCCO>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]2[S:21][C:20](=[NH:19])[NH:22][C:13]2=[O:15])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 3-(4-acetonylphenyl)-2-chloropropionate, ethylene ketal (4.86 g), thiourea (1.19 g) and sodium acetate (1.29 g) in 2-methoxyethanol (25 ml) was stirred and heated at 100 ° C. for 16 h. The solvent was evaporated and the residue was diluted with 50:50 water/hexane (50 ml). The resulting solid was filtered, dried and purified by chromatography on silica gel. Elution with methanol:chloroform (4:96) gave 5-(4-acetonylbenzyl)-2-iminothiazolidine-4-one as a white solid, mp 196°-198° C.

Workup

customThe solvent was evaporated
additionthe residue was diluted with 50:50 water/hexane (50 ml)
filtrationThe resulting solid was filtered
customdried
custompurified by chromatography on silica gel
washElution with methanol:chloroform (4:96)

Sources & evidence

ORD record: ord-bb349535f3ec4478b78abd87796325f1
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05153210

Reaction notes

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