122717-93-5

Basic information

• Product Name: 2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide
• Synonyms: 2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide
• CAS NO: 122717-93-5
• Molecular Weight: 236.338
• Mol File: 122717-93-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide(122717-93-5)
• EPA Substance Registry System: 2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide(122717-93-5)

Safety Data

• Hazardous Substances Data: 122717-93-5(Hazardous Substances Data)

Upstream product

• 156-57-0 2-mercaptoethylamine hydrochloride 
• 102-01-2 N-phenylacetoacetamide 
• 60-23-1 Cysteamine 

Downstream Products

• 122718-01-8 4-acetyl-5,6-dihydro-3-methyl-N-phenyl-1,4-thiazine-2-carboxamide 
• 122718-03-0 2-(4-Acetyl-5,6-dihydro-4H-[1,4]thiazin-3-yl)-N-phenyl-acetamide 
• 122717-95-7 2-(3-Acetyl-2-methyl-thiazolidin-2-yl)-N-phenyl-acetamide 
• 122717-97-9 trans-3-acetyl-2-methyl-2-(N-phenylcarbamoylmethyl)-1,3-thiazolidine 1-oxide 
• 122717-97-9 cis-3-acetyl-2-methyl-2-(N-phenylcarbamoylmethyl)-1,3-thiazolidine 1-oxide 

Relevant articles and documents

Thermal rearrangement of 1,3-thiazolidine sulfoxides: Thiolsulfinate and thioaldehyde intermediates

Stereospecific ring opening of the sulfoxides cis-13 and trans-14 in refluxing toluene gave the corresponding sulfenic acids 9, 10 intermediates respectively. The sulfenic acid 9 dimerized to the thiolsulfinate 17 by dual function of the sulfenic acid as S-nucleophile/S-electrophile with loss of water while the sulfenic acid 10 was unchanged. The stereospecific recyclization of 10 to the parent sulfoxide 14 increases the higher pi- electron density of the double. The thermolysis of the thiolsulfinate 17 gave the transient sulfenic acid 9, which dimerized again to repeat the process and unisolable thioaldehyde 21. The thioaldehyde 21 was converted to either pyrrole 15 by the action of a sulfinic acid 20 catalyst formed inevitably by hydrolysis of 17 under the reaction conditions, or thiazole 18 under neutral conditions. In these rearrangements, the amide carbonyl group facilitated the elimination of a neighboring hydrogen.

Rearrangement of 1,3-Thiazolidine Sulfoxides

Oxidation of 1,3-thiazolidines 3 gave a mixture of cis- and trans-sulfoxides 4 and 5, major and minor, respectively.In the presence of an acid catalyst both the cis and trans sulfoxides underwent ring expansion reaction to produce dihydro-1,4-thiazines 2