Toluene → HCID 54366486, compound

HRID 330529Notes

Reaction equation

[S:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].[C:8]([C:12]1[CH:13]=[C:14]([CH:20]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:22]=1[OH:23])[CH:15]=CC(=O)C)([CH3:11])([CH3:10])[CH3:9].C([O-])(=O)C.[NH4+].[C:33]1(C)[CH:38]=CC=C[CH:34]=1>>[CH3:34][C:33](=[CH:15][C:14]1[CH:13]=[C:12]([C:8]([CH3:9])([CH3:11])[CH3:10])[C:22]([OH:23])=[C:21]([C:24]([CH3:26])([CH3:25])[CH3:27])[CH:20]=1)[CH:38]=[C:7]1[S:1][C:2](=[S:3])[NH:4][C:5]1=[O:6]

Participants

Reactant 4

HCID 1140Toluene

HCID 215849HCID 215849, compound

HCID 517165Ammonium Acetate

HCID 1201546Rhodanine

Product 1

HCID 54366486HCID 54366486, compound

Procedure

A mixture of 1.20 g (0.009 mol) of rhodanine, 1.64 g (0.006 mol) of 3,5-di-t-butyl-4-hydroxybenzalacetone, 0.23 g (0.003 mol) of ammonium acetate and 5 of toluene was heated under reflux for 7 hours. After cooling, the precipitated crystals were recovered by filtration, washed with water and further methanol to give 0.18 g of the desired 5-(α-methyl-3,5-di-t-butyl-4-hydroxycinnamylidene)-4-oxo-2-thioxothiazolidine.

Workup

temperaturewas heated
temperatureunder reflux for 7 hours
temperatureAfter cooling
filtrationthe precipitated crystals were recovered by filtration
washwashed with water and further methanol

Sources & evidence

ORD record: ord-4f763247b0884520814cdafd7fe940ea
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04897406

Reaction notes

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