4-Thiazolidinone, 3-methyl-2-thioxo- → 5-[[4-[(4-Acetyl-3-hydroxy-2-propylphenyl)methoxy]phenyl]methylene]-3-methyl-2-thioxo-4-thiazolidinone

HRID 1069120

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)=[C:6]([CH2:20][CH2:21][CH3:22])[C:5]=1[OH:23])(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].[CH3:29][N:30]1[C:34](=[O:35])[CH2:33][S:32][C:31]1=[S:36]>C(O)(=O)C>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[C:33]3[S:32][C:31](=[S:36])[N:30]([CH3:29])[C:34]3=[O:35])=[CH:14][CH:13]=2)=[C:6]([CH2:20][CH2:21][CH3:22])[C:5]=1[OH:23])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Under a nitrogen atmosphere in a three-neck round bottom flask 4-[(4-acetyl-3-hydroxy-2-propylphenyl)methoxy]benzaldehyde (90.0 mg, 0.29 mmol) was dissolved in acetic acid (1.5 ml) with stirring. To this solution was added sodium acetate (82.8 mg, 1.00 mmol) and N-methylrhodanine (42.5 mg, 0.29 mmol). The reaction mixture was then heated to 100° C. and maintained at this temperature for about two hours at which time the reaction mixture was raised to the reflux temperature and allowed to reflux for about 28 hours. The reaction progress was monitored by thin layer chromatography.

Workup

temperaturemaintained at this temperature for about two hours at which time the reaction mixture
temperaturewas raised to the reflux temperature
temperatureto reflux for about 28 hours

Sources & evidence

ORD record: ord-03a655ea75a4460ca91808761dd55d17
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06251928B1

Linked notes

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