Beta-Alanine → (Z)-5-[[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]methylene]-2-thioxo-4-thiazolidinone

HRID 1885226Notes

Reaction equation

HRID 1885226 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=O.[S:19]1[CH2:25][C:23](=[O:24])[NH:22][C:20]1=[S:21].NCCC(O)=O>C(O)(=O)C>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1/[CH:13]=[C:25]1/[C:23](=[O:24])[NH:22][C:20](=[S:21])[S:19]/1

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 1201546RhodanineHCID 150273772-[(2,6-Dichloro-3-methylphenyl)amino]benzaldehyde

Product 1

HCID 9822030(Z)-5-[[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]methylene]-2-thioxo-4-thiazolidinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a room temperature solution of 2-[(2,6-dichloro-3-methylphenyl)amino]benzaldehyde (209 mg, 0.75 mmols) and rhodanine (104 mg, 0.78 mmols) in 15 mL of acetic acid is added β-alanine (48 mg, 0.54 mmols). The solution is heated at reflux for one hour. During this time a thick precipitate forms. The mixture is filtered hot, washing with an additional 5 mL of [[2- [(2,6-dichloro-3-methylphenyl)amino]phenyl]methylene]-2-thioxo-4-thiazolidinone as a fluffy orange solid; mp 274°-276° C. dec.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for one hour
  3. filtrationThe mixture is filtered hot
  4. washwashing with an additional 5 mL of [[2- [(2,6-dichloro-3-methylphenyl)amino]phenyl]methylene]-2-thioxo-4-thiazolidinone as a fluffy orange solid

Sources & evidence

ORD record
ord-c260297bc3c64de1aee85150d1d10784
Source dataset
uspto-grants-1992_09
Patent number
US05143929

Reaction notes

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