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

HRID 1885228Notes

Reaction equation

HRID 1885228 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.C[N:20]1[C:24](=[O:25])[CH2:23][S:22][C:21]1=[S:26].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:23]1/[C:24](=[O:25])[NH:20][C:21](=[S:26])[S:22]/1

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 729004-Thiazolidinone, 3-methyl-2-thioxo-HCID 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-thiazolidinoneYield 65.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a room temperature solution of 2-[(2,6-dichloro-3-methylphenyl)amino]benzaldehyde (276 mg, 0.99 mmols) and 3-methylrhodanine (166 mg, 1.13 mmols) in 15 mL of acetic acid is added β-alanine (102 mg, 1.14 mmols). The solution is heated at reflux for 3.5 h. The solution is cooled to room temperature and the resulting precipitate is collected by filtration to provide 258 mg (64%) of (Z)-5-[[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]methylene]-2-thioxo-4-thiazolidinone as a bright orange solid; mp=175°-176° C. Calc'd for C18H14Cl2N2OS2:

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 3.5 h
  3. filtrationthe resulting precipitate is collected by filtration

Sources & evidence

ORD record
ord-b32f909409c74039bc80a4e85e51b09a
Source dataset
uspto-grants-1992_09
Patent number
US05143929

Reaction notes

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