504-78-9

Usage

Uses

1. Used in Pharmaceutical Industry:
Thiazolidine is used as a synthetic building block for the development of various pharmaceutical compounds. Its unique chemical structure allows for the creation of novel molecules with potential therapeutic applications.
2. Used in Polymer Synthesis:
Thiazolidine is used as a monomer in the synthesis of homogeneous penicillamine disulfide cross-linked polypeptides. These polypeptides have potential applications in the development of new materials with specific properties, such as enhanced stability or biocompatibility.
3. Used in Chemical Research:
Due to its reversible formation and lability towards hydrolysis, Thiazolidine serves as an important model compound in chemical research. It helps scientists understand the behavior of similar heterocyclic compounds and their interactions with other molecules, which can be crucial in the development of new drugs and materials.

InChI:InChI=1/C3H7NS/c1-2-5-3-4-1/h4H,1-3H2/p+1

Synthetic route

formaldehyd (50-00-0) + 2-mercaptoethylamine hydrochloride (156-57-0) → 1,3-thiazolidine (504-78-9)

formaldehyd (50-00-0) + Cysteamine (60-23-1) → 1,3-thiazolidine (504-78-9)

Conditions	Yield
With phosphate buffer In water at 25℃; for 0.5h;

formaldehyd (50-00-0) + Cysteamine (60-23-1) → 1,3-thiazolidine (504-78-9) + 4,5-dihydro-thiazole (504-79-0)

Conditions	Yield
With phosphate buffer at 25℃; for 0.5h; Mechanism; var. buffer systems; var. aldehydes; also in the presence of ethanol;

1,3-thiazolidine (504-78-9) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl thiazolidine-3-carboxylate (148312-55-4)

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 20h;	100%
In tetrahydrofuran; water at 20℃; for 20h; Schlenk technique;	99%
With dmap In acetonitrile for 3h; Ambient temperature;	89%
In 1,4-dioxane; water	86.2%

1,3-thiazolidine (504-78-9) + 2,6-Dichloro-4-morpholino-1,3,5-triazine (6601-22-5) → 2-chloro-4-morpholino-6-(3-thiazolidinyl)-1,3,5-triazine

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide a) -5 deg C, 2 h, b) RT, 20 h;	97%
With potassium carbonate In hexane; ethyl acetate; N,N-dimethyl-formamide	97.2%

1,3-thiazolidine (504-78-9) + (S)-[1-(3-hydroxyadamantan-1-yl)-2-oxo-2-pyrrolidin-1-ylethyl]-carbamic acid tert-butyl ester (841302-34-9) → (S)-[1-(3-hydroxyadamantan-1-yl)-2-oxo-2-thiazolidin-3-ylethyl]-carbamic acid tert-butyl ester (841302-35-0)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In DMF (N,N-dimethyl-formamide) at 0℃; for 22h;	95.7%

1,3-thiazolidine (504-78-9) + benzoyl chloride (98-88-4) → N-benzoyl-1,3-thiazolidine (941599-07-1)

Conditions	Yield
In dichloromethane at 0℃; for 0.75h;	95%

1,3-thiazolidine (504-78-9) + 2-chloro-5-cyano-6-ethoxy-4-phenylpyridine-3-carboxaldehyde (143815-60-5) → 2-Ethoxy-5-formyl-4-phenyl-6-thiazolidin-3-yl-nicotinonitrile (143815-68-3)

Conditions	Yield
With triethylamine In tetrahydrofuran for 0.166667h; Heating;	93%

1,3-thiazolidine (504-78-9) + trifluoroacetic acid (76-05-1) + N-Boc pyroglutamic acid-Wang resin → (S)-2-Amino-5-oxo-5-thiazolidin-3-yl-pentanoic acid; compound with trifluoro-acetic acid

Conditions	Yield
Stage #1: 1,3-thiazolidine; N-Boc pyroglutamic acid-Wang resin In tetrahydrofuran Addition; Stage #2: trifluoroacetic acid In water for 2.5h; Hydrolysis;	93%

1,3-thiazolidine (504-78-9) + (S)-tert-butoxycarbonylamino-(trans-4-hydroxy-cyclohexyl)-acetic acid (336870-02-1) → (S)-[1-(4-hydroxy-cyclohexyl)-2-oxo-2-thiazolidin-3-yl-ethyl]-carbamic acid tert-butyl ester

Conditions	Yield
Stage #1: (S)-tert-butoxycarbonylamino-(trans-4-hydroxy-cyclohexyl)-acetic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In Isopropyl acetate at 0℃; for 2h; Stage #2: 1,3-thiazolidine In Isopropyl acetate at 0 - 20℃; for 18h;	93%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 12h;

1,3-thiazolidine (504-78-9) + 3-((2R,3S,4R,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-propionic acid pentafluorophenyl ester (682349-94-6) → Acetic acid (2R,3R,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(3-oxo-3-thiazolidin-3-yl-propyl)-tetrahydro-pyran-4-yl ester

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	92%

1,3-thiazolidine (504-78-9) + 4-nitro-benzoyl chloride (122-04-3) → N-(4-nitrobenzoyl)-1,3-thiazolidine

Conditions	Yield
In dichloromethane at 0℃; for 0.75h;	92%
With triethylamine In dichloromethane

1,3-thiazolidine (504-78-9) + (E)-β-methylcinnamaldehyde (1196-67-4, 21878-52-4, 21866-70-6) → (R)-3-phenyl-1-(thiazolidin-3-yl)butan-1-one

Conditions	Yield
Stage #1: (E)-β-methylcinnamaldehyde With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; BF4(1-)*C21H22N3O(1+); 1,1'-biphenyl-2,2'-diyl hydrogen phosphate In toluene at 40℃; for 14h; Molecular sieve; Sealed tube; Inert atmosphere; Stage #2: 1,3-thiazolidine In toluene at 20℃; for 10h; Molecular sieve; Sealed tube; Inert atmosphere; enantioselective reaction;	92%

1,3-thiazolidine (504-78-9) + di-tert-butyl dicarbonate (24424-99-5) + 1-aminocyclohexanecarboxylic acid benzyl ester (102373-23-9) → 1-[[(3-thiazolidinylcarbonyl)]amino]cyclohexanecarboxylic acid benzyl ester

Conditions	Yield
Stage #1: di-tert-butyl dicarbonate; 1-aminocyclohexanecarboxylic acid benzyl ester With dmap In dichloromethane at 20℃; for 0.666667h; Stage #2: 1,3-thiazolidine With triethylamine In dichloromethane at 20℃; for 19h;	91%

1,3-thiazolidine (504-78-9) + propargyl bromide (106-96-7) → thiazolidino-3 propyne-1 (85670-81-1)

Conditions	Yield
With sodium carbonate	90%
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 4h;

1,3-thiazolidine (504-78-9) + N-(4-chloro-6-methyl-pyrimidin-2-yl)-N'-(3-trifluoromethyl-phenyl)-guanidine → N-(4-methyl-6-thiazolidin-3-yl-pyrimidin-2-yl)-N'-(3-trifluoromethyl-phenyl)-guanidine

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 100℃; for 16h;	90%

1,3-thiazolidine (504-78-9) + (2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid (59969-65-2) → (2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid thiazolidide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 4 - 20℃;	90%

1,3-thiazolidine (504-78-9) + (S)-3-(4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)phenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid (114346-31-5) → C32H35N3O5S (937207-80-2)

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran at 0 - 20℃; for 8h;	90%

1,3-thiazolidine (504-78-9) + (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate (102195-80-2) → (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester (401564-36-1)

Conditions	Yield
With acetic acid In methanol at 0 - 30℃; for 2.5h; Large scale;	90%

1,3-thiazolidine (504-78-9) + (R)-7-[3-tertbutoxycarbonylamino-4-(2,4,5-tri-fluorophenyl)butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid (1174039-19-0) → (R)-[3-oxo-3-[1-(thiazolidine-3-carbonyl)-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl]-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester (1174039-38-3)

Conditions	Yield
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 20℃; for 2h;	89%

1,3-thiazolidine (504-78-9) + carbon disulfide (75-15-0) + 2,3-bis(chloromethyl)-1,4-naphthoquinone (31581-11-0) → 3-(thiazolidin-3-carbothioyl)thiomethyl-(1,4-dioxo-1,4-dihydronaphthalene-2-yl)methyl thiazolidin-3-carbodithioate

Conditions	Yield
Stage #1: 1,3-thiazolidine; carbon disulfide In acetonitrile at 20℃; for 0.5h; Stage #2: 2,3-bis(chloromethyl)-1,4-naphthoquinone In acetonitrile at 20℃; for 48h;	88.8%

1,3-thiazolidine (504-78-9) + 1-Naphthylacetyl-thioproline (88329-34-4, 122230-50-6) → (1-Naphthyl)acetyl-Thiopro-thiazolidine (122230-45-9)

Conditions	Yield
With dicyclohexyl-carbodiimide	88%

1,3-thiazolidine (504-78-9) + (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid (115962-35-1, 144069-68-1, 78879-20-6) → 3-(thiazolidine-3-carbonyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (460086-07-1)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1.5h;	88%

1,3-thiazolidine (504-78-9) + phenylbutyric acid chloride (18496-54-3) → N-(4-phenylbutanoyl)thiazolidine (127401-86-9)

Conditions	Yield
With sodium chloride; triethylamine In dichloromethane	88%

1,3-thiazolidine (504-78-9) + S-6-bromohexanoic acid N-α-methylbenzylamide (78461-93-5) → S-6-(3-thiazolidinyl)hexanoic acid N-α-methylbenzylamide (78461-95-7)

Conditions	Yield
With triethylamine In isopropyl alcohol for 6h; Heating;	87%

1,3-thiazolidine (504-78-9) + R-6-bromohexanoic acid N-α-methylbenzylamide (78461-92-4) → R-6-(3-thiazolidinyl)hexanoic acid N-α-methylbenzylamide (78461-94-6)

Conditions	Yield
With triethylamine In isopropyl alcohol for 6h; Heating;	87%

1,3-thiazolidine (504-78-9) + (2S,4S)-1-tert-butoxycarbonyl-4-ethoxycarbonyl-2-pyrrolidinecarboxylic acid (898273-26-2) → 1-tert-butyl 3-ethyl (3S,5S)-5-(1,3-thiazolidin-3-ylcarbonyl)-1,3-pyrrolidinedicarboxylate (1019637-84-3)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 19h;	86%

1,3-thiazolidine (504-78-9) + Boc-Cys(Npys)-OH → C17H24N4O5S3

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran at 0 - 20℃; for 4h;	86%

1,3-thiazolidine (504-78-9) + N-tert-butoxycarbonyl-4-oxo-L-proline (84348-37-8) → (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester (401564-36-1)

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 2 - 7℃; for 2h; Large scale;	86%
Stage #1: N-tert-butoxycarbonyl-4-oxo-L-proline With pivaloyl chloride; N-ethyl-N,N-diisopropylamine In ethyl acetate at 10℃; for 0.5h; Large scale; Stage #2: 1,3-thiazolidine In ethyl acetate at 0 - 10℃; for 1h; Reagent/catalyst; Temperature; Solvent; Large scale;	86%
Stage #1: N-tert-butoxycarbonyl-4-oxo-L-proline With dicyclohexyl-carbodiimide In toluene at -10 - -5℃; Stage #2: 1,3-thiazolidine With dmap In toluene at -6 - 5℃; for 1.33333h;	81.7%
With dmap; dicyclohexyl-carbodiimide In toluene at -6 - 5℃; for 1.33333h;	81.7%
Stage #1: N-tert-butoxycarbonyl-4-oxo-L-proline With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In toluene at 0℃; for 3h; Large scale; Stage #2: 1,3-thiazolidine With dmap at 0℃; for 2h; Reagent/catalyst; Large scale;	50 kg

1,3-thiazolidine (504-78-9) + benzene 1,3-dicarboxylic acid monomethyl ester (1877-71-0) → methyl 3-(thiazolidine-3-carbonyl)benzoate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 18h;	85%

1,3-thiazolidine (504-78-9) + C18H18N2O5S → C21H23N3O4S2

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 24h;	83%

1,3-thiazolidine (504-78-9) + α-bromoacetophenone (70-11-1) → 3-(benzoylmethyl)thiazolidine (133914-09-7)

Conditions	Yield
With potassium carbonate In ethanol	82%

1,3-thiazolidine (504-78-9) + (S)-{trans-4-[(3-amino-pyrazine-2-carbonyl)-amino]-cyclohexyl}-tert-butoxycarbonylamino-acetic acid (867212-43-9) → (S)-(1-{trans-4-[(3-amino-pyrazine-2-carbonyl)-amino]-cyclohexyl}-2-oxo-2-thiazolidin-3-yl-ethyl)-carbamic acid tert-butyl ester (867212-44-0)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h;	82%

Upstream product

• 50-00-0 formaldehyd 
• 156-57-0 2-mercaptoethylamine hydrochloride 
• 60-23-1 Cysteamine 

Downstream Products

• 874509-58-7 3-(4-nitro-benzenesulfonyl)-thiazolidine 
• 50916-02-4 3-(4-acetoxy-3,5-dimethoxy-benzoyl)-thiazolidine 
• 50916-00-2 3-(3,4,5-Trimethoxybenzoyl)thiazolidin 
• 10061-40-2 2-(methylamino)ethanethiol 
• 117769-01-4 3-(p-cyanophenylazo)-1,3-thiazolidine 
• 117769-04-7 3-(p-chlorophenylazo)-1,3-thiazolidine 
• 124256-01-5 7-(2-aminoethyl)thio-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 117769-02-5 3-(p-nitrophenylazo)-1,3-thiazolidine 
• 134591-59-6 3-<(1-Z-pyrrolidine-2-yl)methyl>thiazolidine 
• 122230-40-4 4-Phenylbutyryl-Thiopro-thiazolidine 
• 134563-20-5 Z-Thiopro (S-oxide)-thiazolidine 
• 99507-82-1 3-[2-(2-Methoxy-phenoxy)-ethyl]-thiazolidine 
• 117769-03-6 3-(p-methoxycarbonylphenylazo)-1,3-thiazolidine 
• 38613-29-5 3-[2-chloro-4-(3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-benzenesulfonyl]-thiazolidine 

Relevant academic research and scientific papers

Development of a compound-specific carbon isotope analysis method for atmospheric formaldehyde via NaHSO3 and cysteamine derivatization

A novel method has been developed for the compound-specific carbon isotope analysis of atmospheric formaldehyde using gas chromatography/combustion/isotope ratio mass spectrometry (GC/C/IRMS). The method allows the determination of the δ13C value for atmospheric formaldehyde at nanogram levels with higher precision and lower detection limit. In the present work, atmospheric formaldehyde was collected using NaHSO3-coated Sep-Pak silica gel cartridges, washed out by water, then derivatized by cysteamine of known δ13C value, and the δ13C value of its derivative (thiazolidine) determined by GC/C/IRMS. Finally, the δ13C value of atmospheric formaldehyde could be calculated by a simple mass balance equation between formaldehyde, cysteamine, and thiazolidine. Using three formaldehydes with different δ13C values, calibration experiments were carried out over large ranges of formaldehyde concentrations. The carbon isotope analysis method achieved excellent reproducibility and high accuracy. There was no carbon isotopic fractionation throughout the derivatization processes. The differences in the carbon isotopic compositions of thiazolidine between the measured and predicted values were always 13C values of atmospheric formaldehyde were different during the daytime and nighttime. This method proved suitable for the routine operation and may provide additional insight on sources and sinks of atmospheric formaldehyde.

Structural determination and odor characterization of N-(2-mercaptoethyl)-1,3-thiazolidine, a new intense popcorn-like-smelling odorant

The chemical structure of a novel, roasty, popcorn-like-smelling aroma compound formed from the reaction of fructose with cysteamine was studied by high-resolution mass spectrometry and nuclear magnetic resonance experiments. The structure of N-(2-mercaptoethyl)-1,3-thiazolidine exhibiting the extremely low odor threshold of 0.005 ng/L in air was finally confirmed by synthesis.

Process for the preparation of teneligliptin

A process for the preparation of teneligliptin.

Facile synthesis of a family of H8BINOL-amine compounds and catalytic asymmetric arylzinc addition to aldehydes

A family of optically active H8BINOL-AM compounds containing 3,3′-bis-tertiary amine substituents are synthesized by using a one-step reaction of H8BINOL with amino methanols that were in situ generated from various cyclic or acyclic secondary amines and paraformaldehyde. The H 8BINOL-AM compounds are used to catalyze the reaction of functional arylzincs, in situ prepared from the reaction of aryliodides with ZnEt 2, with aldehydes to produce chiral diaryl carbinols and a few arylalkyl carbinols. Through this study, highly enantioselective catalysts were identified. It was found that the H8BINOL-AM compounds with sterically less congested cyclic or acyclic amino methyl substituents were more enantioselective than those with more bulky substituents. The pyrrolidinyl derivative (S)-12 in most cases showed greater enantioselectivity than other H8BINOL-AM compounds, especially for the challenging ortho-substituted aromatic aldehydes. A H8BINOL-AM with 3,3′-bis-sec-amine substituents, prepared by a multistep method, was also used to catalyze the arylzinc addition to aldehydes, but it showed enantioselectivity lower than that of the compounds with tertiary amine groups. It was found for the first time that an aryl bromide, 2-bromothiophene, could be used to prepare an arylzinc reagent by reaction with ZnEt2. The addition of this heteroarylzinc reagent to an aldehyde in the presence of (S)-12 proceeded with good enantioselectivity.

2-aminopyridine derivatives and combinatorial libraries thereof

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14-substituted marcfortines and derivatives useful as antiparasitic agents

There are disclosed 14α-hydroxymarcfortine derivatives of the natural products marcfortine A, B, C, and D useful in the treatment and prevention of helminth and arthropod infections of animals and plants. The synthetic derivatives are of Formula (I). STR1

Marcfortine/paraherquamide derivatives useful as antiparasitic agents

There are disclosed 18-thiomarcfortine derivatives of the natural products marcfortine A, B and C, C-18 thioparaherquamide and derivatives thereof, novel N-1 marcfortines A, B, and C and derivatives thereof, novel N-1 paraherquamide and derivatives thereof usefull in the treatment and prevention of helninth and arthropod infections of animals and plants. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Examiner Robert T. Bond whose telephone number is (703)308-4711. The examiner can normally be reached on Monday through Friday from 8:00 AM to 4:30 PM.

Scavenger assisted combinatorial process for preparing libraries of amides, carbamates and sulfonamides

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Mechanistic Studies on Thiazolidine Formation in Aldehyde/Cysteamine Model Systems

A mechanism was proposed to elucidate the formation of a thiazolidine in aldehyde/cysteamine model systems. Buffer dramatically promotes thiazolidine formation from formaldehyde and cysteamine. Phosphate tends to stabilize the primary carbocation formed, and this may lead to completion of the cyclization by attack of the amino nitrogen on the activated carbon. Protic solvent, by removing the water molecule, further enhances thiazolidine formation. Redox reaction catalyzed by phosphate ions results in the conversion of thiazolidine to the corresponding thiazoline through hydride transfer.

Antiatherosclerotic and antithrombotic 1-benzopyran-4-ones and 2-amino-1,3-benzoxazine-4-ones

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