Beta-Alanine → HCID 19880352, compound

HRID 1885227Notes

Reaction equation

HRID 1885227 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=O)[CH:6]=[CH:7][CH:8]=1.[S:20]1[CH2:26][C:24](=[O:25])[NH:23][C:21]1=[S:22].NCCC(O)=O>C(O)(=O)C>[S:22]=[C:21]1[NH:23][C:24](=[O:25])/[C:26](=[CH:12]/[C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:19])([F:18])[F:1])[CH:4]=2)/[S:20]1

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 1201546RhodanineHCID 12292418HCID 12292418, compound

Product 1

HCID 19880352HCID 19880352, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a room temperature solution of 2-[[3-(trifluoromethyl)phenyl]amino]benzaldehyde (749 mg, 2.83 mmols) and rhodanine (398 mg, 2.99 mmols) in 20 mL of acetic acid is added β-alanine (382 mg, 4.29 mmols). The solution is heated at reflux for 45 min. During this time a thick precipitate forms. The mixture is filtered hot, washing with an additional 10 mL of acetic acid, to provide 715 mg (66%) of (Z)-2-thioxo-5-[[2-[[3-(trifluoromethyl)phenyl]amino]phenyl]methylene]-4-thiazolidinone as a bright red-orange solid; mp=234°-236° C. Calc'd for C17H11F3N2OS2:

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 45 min
  3. filtrationThe mixture is filtered hot
  4. washwashing with an additional 10 mL of acetic acid

Sources & evidence

ORD record
ord-5274669f827a4c66b6acb69b84723939
Source dataset
uspto-grants-1992_09
Patent number
US05143929

Reaction notes

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