Thiazolidine

Structural formula
General
Surname	Thiazolidine
other names	1,3-thiazolidine ( IUPAC )
Molecular formula	C 3 H 7 NS
Brief description	colorless liquid
External identifiers / databases
CAS number 504-78-9 EC number 208-002-5 ECHA InfoCard 100.007.275 PubChem 10444 ChemSpider 10013 Wikidata Q413761
properties
Molar mass	89,15 g · mol -1
Physical state	liquid
density	1.13 g cm −3 (25 ° C)
boiling point	72–75 ° C (33 h Pa )
Refractive index	1.551 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 226 P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Thiazolidine is an organic liquid. Due to its structure, it can be considered as N , S - acetal . As an isolated substance it has no notable technical importance, but the basic thiazolidine structure is found in many natural substances and active pharmaceutical ingredients.

properties

In chemistry, the thiazolidine backbone is a five-membered ring with one sulfur and one nitrogen atom in the 1- or 3-position. A number of thiazolidine derivatives are of great importance in medical applications. Thiazolidines are popular as a partial structure of penicillins . But they can also be found in other active ingredients such as rosiglitazone and pioglitazone , both of which are used to treat type II diabetes mellitus .

Manufacturing

The preparation of thiazolidine by reacting 2-aminoethanethiol with formaldehyde was described in 1937 by Hans Thacher Clarke . Accordingly, the 1,3-thiazolidine-4-carboxylic acid is obtained by the reaction of cysteine with formaldehyde. Further substituted thiazolidines are obtained from organic 1-amino-2-mercaptans by reaction with aldehydes or ketones with elimination of water.

Addition reactions at the C = N double bond of 3-thiazolines (see Asinger reaction ) also give thiazolidines.

See also

• Thiazole

Individual evidence

1. ↑ Data sheet thiazolidine from Acros, accessed on March 13, 2010.
2. ↑ ^{a b} Thiazolidine data sheet from AlfaAesar, accessed on March 13, 2010 ( PDF )(JavaScript required) .
3. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-482.
4. ↑ ^{a b} Data sheet Thiazolidine from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
5. ^ Sarah Ratner, HT Clarke: The Action of Formaldehyde upon Cysteine . In: Journal of the American Chemical Society . tape 59 , no. 1 , January 1937, p. 200 , doi : 10.1021 / ja01280a050 .