Acetic Acid → 2-[(4-Oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]benzoic acid

HRID 328975Notes

Reaction equation

HRID 328975 reaction equation
[C:1]([OH:11])(=[O:10])[C:2]1[C:3](=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH:4]=O.[S:12]1[CH2:18][C:16](=[O:17])[NH:15][C:13]1=[S:14].C(O)(=O)C.C([O-])(=O)C.[Na+]>O>[C:1]([C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:18]1[S:12][C:13](=[S:14])[NH:15][C:16]1=[O:17])([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 8406Phthalaldehydic acidHCID 517045Sodium AcetateHCID 1201546Rhodanine

Product 1

HCID 28263832-[(4-Oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a hot stirred solution of 20.5 g. (134 mM) of phthalaldehydic acid and 17.95 g. (135 mM) of rhodanine in 90 ml. of glacial acetic acid is added 36.0 g. (438 mM) of sodium acetate. While heating the resulting solution to reflux, a precipitate forms and an additional 30 ml. of acetic acid is added. After refluxing the mixture for 0.5 hour, it is cooled, poured into water, and filtered to separate a yellow solid. The solid is washed with water and boiled with 500 ml. of isopropanol. The resulting mixture is cooled and filtered to separate 31.14 g. (87.5%) of the 5-o-carboxybenzylidenerhodanine as yellow needles, m.p. 276°-278°.

Workup

  1. temperatureWhile heating the resulting solution
  2. temperatureto reflux
  3. temperatureAfter refluxing the mixture for 0.5 hour
  4. temperatureit is cooled
  5. filtrationfiltered
  6. customto separate a yellow solid
  7. washThe solid is washed with water
  8. temperatureThe resulting mixture is cooled
  9. filtrationfiltered
  10. customto separate 31.14 g

Sources & evidence

ORD record
ord-60b9b158faa14c3cbfc315c585947803
Source dataset
uspto-grants-1977_04
Patent number
US04018891

Reaction notes

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