Girard, M. L. published the artcileStructural and reactional possibilities of thiazolidine derivatives. I. Addition, substitution, and hydrolysis, Related Products of thiazole, the publication is Bulletin de la Societe Chimique de France (1968), 3461-8, database is CAplus.
The reactivities of 2-imino-4-thiazolidinone (pseudothiohydantoin) (Ia), 2-4-thiazolidinedione (Ib), and 2-thio-2,4-thiazolidinedione (rhodanine) (Ic) were studied and some of their derivatives prepared by original or improved techniques and studied by thin layer chromatog., uv, ir, and polarography for structural determinations The hydrolytic ring cleavage was also investigated. E.g., addition reactions in the 2-position were attempted. A saturated solution of Ic in absolute EtOH was treated with saturated KOH in absolute EtOH to the exact equivalence point observed with a potentiometer to precipitate 90% K salt (II) of Ic. The K salt of the 2-thiohydantoin was obtained similarly (80%) in 8:2 EtOH-HCONMe2. II stirred in dilute EtOH during 2 hrs. with Me2SO4 gave yellow 2-(methylthio)-2-thiazolin-4-one, m. 170°. Stirring II in 90% EtOH with an equimol. amount of benzyl chloride at room temperature for 24 hrs. gave 2-(benzylthio)-2-thiazolin-4-one, yellowish brown, m. 65°. 2-(Acetylthio)-2-thiazolin-4-one (III), m. 250° (decomposition) was obtained by reaction of II in aqueous solution with an equimol. amount of ClCH2CO2H. Stirring ClCH2CO2K in dilute EtOH with an equimol. amount of II 1 hr. also gave III. Ic was converted into Ib by refluxing with 20% HNO3. 3-Substituted rhodanines (IIIa) were prepared via the dithiocarbamate by an improved method. ClCH2CO2K was added to a mixture of 24% aqueous NH3, CS2, and a primary amine, EtOH added, and the mixture acidified and refluxed to precipitate the following IIIa (3-substituent, m.p., and starting amine given): phenyl, 194°, aniline; benzyl, 85°, benzylamine; p-nitrophenyl, 144°, p-nitroaniline. 3-Methylrhodanine, 3-aminorhodanine and N-rhodanineacetic acid were prepared according to published methods. The following 5-substituted derivatives of Ib, Ic, and 3-phenyl-4-thiazolidinone (IV) were obtained by condensation with aldehydes (5-substituent, parent, m.p., and reactants given): benzylidene, Ic, 202°, Ic and BzH; benzylidene, 3 phenylrhodanine, 186°, BzH and 3 phenylrhodanine; p-nitrobenzylidene, Ic, 270°, p-nitrobenzaldehyde and Ic; p-methoxybenzylidene, Ic, 245°, Ic and anisaldehyde; cinnamylidene, Ic, 216°, Ic and cinnamaldehyde; cyclohexylidene, Ic, 173°, Ic and cyclohexanone; butylidene Ic, -, Ic and butyraldehyde; heptylidene, Ic, -, Ic and heptanal; benzylidene, 2,4-thiazolidinedione, 243°, BzH and Ib; benzylidene, 2 imino-4-thiazolidinone, 230° (decomposition), Ia and BzH; benzylidene, IV, 205°, BzH and IV. Electrochem. study of the hydrolytic cleavage of the rhodanine derivatives suggested the following preparation of α-mercaptocinnamic acid (VI): V (1 mole) dissolved in 200 ml. 2M Me4NOH solution, was kept 48 hrs. at room temperature and acidified with HCl to precipitate 80% yellow VI, m. 124° (ethanol).
Bulletin de la Societe Chimique de France published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Related Products of thiazole.
Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica