thiazolidine

Also known as tetrahydrothiazole, 1-thia-3-azacyclopentane

Thiazolidine is a heterocyclic organic compound with the formula (CH2)3(NH)S. It is a 5-membered saturated ring with a thioether group and an amine group in the 1 and 3 positions. It is a sulfur analog of oxazolidine. Thiazolidine is a colorless liquid. Although the parent thiazolidine is only of academic interest, some derivatives, i.e., the thiazolidines, are important, such as the antibiotic penicillin.

Chemical data

Formula: C3H7NS
Molecular weight: 89.16 g/mol
IUPAC name: 1,3-thiazolidine
SMILES: C1CSCN1
InChIKey: OGYGFUAIIOPWQD-UHFFFAOYSA-N
XLogP: 0.3
Polar surface area: 37.3 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

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Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 89.03

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Commons category: Thiazolidine
chemical formula: C₃H₇NS
canonical SMILES: C1CSCN1

Sources (3)

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Encyclopedic overview

5 sections

Contents

Preparation
Derivatives
Ring-chain equilibria
See also
References

==Preparation== Thiazolidine is prepared by the condensation of cysteamine and formaldehyde. Other thiazolidines may be synthesized by similar condensations. A notable derivative is 4-carboxythiazolidine (thioproline), derived from formaldehyde and cysteine. The 2-oxo-thiazolidine procysteine is produced from phosgenation of cysteine.

Excerpted from Wikipedia’s “thiazolidine” article, available under the CC BY-SA 4.0 licence.