105774-63-8

Basic information

• Product Name: 4-Thiazolidinone, 3-(4-methoxyphenyl)-2-phenyl-
• CAS NO: 105774-63-8
• Molecular Formula: C16H15NO2S
• Molecular Weight: 285.367
• Mol File: 105774-63-8.mol

Chemical Properties

• CAS DataBase Reference: 4-Thiazolidinone, 3-(4-methoxyphenyl)-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thiazolidinone, 3-(4-methoxyphenyl)-2-phenyl-(105774-63-8)
• EPA Substance Registry System: 4-Thiazolidinone, 3-(4-methoxyphenyl)-2-phenyl-(105774-63-8)

Safety Data

• Hazardous Substances Data: 105774-63-8(Hazardous Substances Data)

Upstream product

• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 68-11-1 mercaptoacetic acid 
• 100-52-7 benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 126079-79-6 <α-(p-methoxyanilino)benzylthio>acetic acid 

Relevant articles and documents

Visible-light-promoted C[sbnd]N and C[sbnd]S bonds formation: A catalyst and solvent-free photochemical approach for the synthesis of 1,3-thiazolidin-4-ones

A visible-light-induced, one-pot mild and efficient, multicomponent-tandem synthesis of diversified 1,3-thiazolidin-4-ones under catalyst and solvent-free conditions is reported. Here, visible-light, an ideal source of energy, has been used as photochemic

Preparation of thiazolidin-4-one derivatives using ZnO–NiO–NiFe2O4 nano-composite system

The hydrothermal synthesis of ZnO–NiO–NiFe2O4 nano-composite is reported. The sample was utilized to characterize via XRD, FE-SEM, EDS, FT-IR, UV–Vis, and BET techniques. The sample consisted of three different phases as ZnO (hexagonal), NiO (cubic), and NiFe2O4 (cubic) with the average particle size as 34?nm and specific surface area, average pore diameter, and pore volume as 64.35?m2?g?1, 13.02?nm, and 0.201?cm3?g?1, respectively. Catalytic behavior of the nano-composite was investigated on the synthesis of thiazolidin-4-one derivatives under thermal and ultrasonic irradiation condition. Our results show that the catalytic activity of ZnO–NiO–NiFe2O4 nano-composite is much higher than ZnO, NiO, and NiFe2O4 metal oxides. All products were prepared in high yields with short reaction times. In addition, the catalyst was recovered for at least five times.

Silica chloride (SiO2-Cl) catalyzed one pot synthesis of 2,3-disubstituted-thiazolidin-4-one

In this paper, we report one-pot, three-component cyclo condensation of an aldehyde, an amine and thioglycolic acid to form 2,3-disubstituted-thiazolidin-4-one by using supported protic acid (Silica Chloride: SiO2-Cl) catalyst. The catalyst SiO2-Cl is compatible with a variety of aldehydes (aryl/heteroaryl) and the aromatic amines affording 2,3-disubstituted-thiazolidin-4-one analogs in 72–89% yields. Moreover, the supported catalyst was recycled several times without significant loss of catalytical activity.

Ultrasound assisted, VOSO4 catalyzed synthesis of 4-thiazolidinones: Antimicrobial evaluation of indazole-4-thiazolidinone derivatives

A simple and expedient multicomponent protocol was developed to synthesize 4-thiazolidinones by employing VOSO4 as a catalyst under ultrasonic irradiation. The significant features of this protocol includes shorter reaction time, high yields, low catalyst loading, and also the catalyst can be recovered and reused up to next four cycles without significant loss in catalytic activity. All the synthesized novel indazole compounds were evaluated for their antibacterial and anti-biofilm activities. Compounds 9n, 9o and 9q showed promising activity (MIC value of 3.9 μg/mL) against K. planticola (MTCC 530). They also exhibited significant bactericidal activity against K. planticola (MTCC 530) (MBC value of 15.6 μg/mL). Additionally, 9n, 9o and 9q inhibited biofilm formation (IC50 values ranging between 20.28–20.79 μg/mL) in this organism.

A catalysis study of mesoporous MCM-41 supported Schiff base and CuSO4·5H2O in a highly regioselective synthesis of 4-thiazolidinone derivatives from cyclocondensation of mercaptoacetic acid

Mesoporous MCM-41 supported Schiff base and CuSO4·5H2O shows high catalytic activity in the cyclocondensation of mercaptoacetic acid with imines (or aldehydes and amines) to afford pharmaceutically important thiazolidinone derivatives. The catalytic reactions involving two-components or three-components afforded the desired product in high yields (up to 98% and 99%). Moreover, the catalyst works well with respect to recyclability, giving the product in 85% and 83% yields after recycling six times.

Facile synthesis of 1,3-thiazolidin-4-ones as antitubercular agents

We have developed, highly efficient, one-pot, solvent-free, [Et3NH][HSO4] catalyzed multicomponent reaction protocol for the synthesis of 1,3-thiazolidin-4-ones in excellent yields. For the first time, the 1,3-thiazolidin-4-ones were evaluated in vitro for their antimycobacterial activity against Mycobacterium tuberculosis dormant MTB H37Ra and Mycobacterium bovis BCG strains. Among the synthesized basic 1,3-thiazolidin-4-ones, particularly the compounds 4c, 4d, 4e, 4f, 4h, 4i and 4j displays promising antitubercular activity along with no significant cytotoxicity against the cell lines MCF-7, A549 and HCT-116.

A facile and effective procedure for the synthesis of 4-thiazolidinone derivatives using Y(OTf)3 as catalyst

ABSTRACT: A one-pot three-component reaction for the synthesis of 4-thiazolidinone derivatives has been established by reacting readily available and inexpensive starting materials of amines, aldehydes and thioglycolic acid using Y(OTf)3 (5 mol%) as catalyst in tetrahydrofuran. This method is very efficient due to low catalyst loading and mild reaction conditions and provides an efficient and promising synthetic strategy for the construction of the thiazolidinone skeleton.

Supported protic acid-catalyzed synthesis of 2,3-disubstituted thiazolidin-4-ones: Enhancement of the catalytic potential of protic acid by adsorption on solid supports

The catalytic potential of various protic acids has been assessed for the one pot tandem condensation-cyclisation reaction involving an aldehyde, an amine, and thioglycolic acid to form 2,3-disubstituted thiazolidin-4-ones. The catalytic potential of the various protic acids that follows the order TfOH > HClO4 > H2SO4 ～ p-TsOH > MsOH ～ HBF4 > TFA ～ AcOH is improved significantly by adsorption on solid supports, in particular using silica gel (230-400 mesh size), with the resulting relative catalytic potential following the order HClO 4-SiO2 > TfOH-SiO2 ? H2SO 4-SiO2 > p-TsOH-SiO2 > MsOH-SiO 2 ～ HBF4-SiO2 > TFA-SiO2 ～ HOAc-SiO2. The better catalytic potential of HClO 4-SiO2 as compared to that of Tf-SiO2, although TfOH is a stronger protic acid than HClO4, can be rationalised through a transition state model depicting the interaction of the individual protic acid with SiO2. The catalytic efficiency of HClO4 adsorbed on various solid supports was in the order HClO4-SiO 2 ? HClO4-K10 > HClO4-KSF > HClO 4-TiO2 ～ HClO4-Al2O3. The catalytic system HClO4-SiO2 is compatible with different variations of aldehydes (aryl/heteroaryl/alkyl/cycloalkyl) and the amines (aryl/heteroaryl/arylalkyl/alkyl/cycloalkyl) affording the desired 2,3-disubstituted thiazolidin-4-ones in 70-87% yields (43 examples). The electronic and the steric factors associated with the aldehydes and the amines provide a handle for selective thiazolidinone formation and were found to be dependent on the extent of imine formation. No significant amount of thiazolidinone formation took place during the reaction of the preformed amide (synthesised from the amine and thioglycolic acid) with benzaldehyde suggesting that the reaction proceeds through the initial reversible imine formation followed by cyclocondensation of the preformed imine with thioglycolic acid, the reversible imine formation being the determining step to control selectivity of thiazolidinone formation in competitive environments. The feasibility of a large scale reaction and catalyst recycling/reuse is demonstrated.

Mass Spectrometric Study of Some 2,3-Diaryl-1,3-thiazolidin-4-ones Under Electron Impact

The mass spectral fragmentations of some 2,3-diaryl-1,3-thiazolidin-4-ones were established by comparing spectra and by using exact mass measurements.The major fragment ions were identified and their relative importances related to substituent effects and

The Formation of 2,3-Disubstituted Thiazolidin-4-ones from S-α'-Aminomercaptoacetic Acid Derivatives

Variously substituted N-benzylidineanilines rapidly react with thioglycolic acid to generate S-α'-aminomercaptoacetic acid derivatives.The latter subsequently cyclize to the corresponding 2,3-diarylthiazolidin-4-ones.Kinetics for the first order cyclization reaction in the solvents toluene, carbon tetrachloride and nitrobenzene have been obtained over the temperature range 333 K to 383 K and are in accord with a neutral, but geometrically complex transition state.