6149-09-3

Upstream product

• 598-52-7 1-(methyl)-thiourea 
• 70-11-1 α-bromoacetophenone 
• 532-27-4 1-chloroacetophenone 
• 74-88-4 methyl iodide 
• 7257-94-5 1-phenyl-2-(p-tolylsulfonyloxy)ethanone 

Downstream Products

• 64949-48-0 N-((Z)-3-methyl-4-phenyl-3H-thiazol-2-ylidene)-thioacetamide 
• 72886-39-6 N-((Z)-3-methyl-4-phenyl-3H-thiazol-2-ylidene)-thiobenzamide 
• 110960-32-2 3-methyl-4-phenyl-2-trifluoroacetylimino-2,3-dihydrothiazole 
• 72886-36-3 N-((Z)-3-methyl-4-phenyl-3H-thiazol-2-ylidene)-benzamide 
• 14269-47-7 N-((Z)-3-methyl-4-phenyl-3H-thiazol-2-ylidene)-acetamide 
• 77459-03-1 (3-methyl-4-phenyl-3H-thiazol-2-ylidene)-phenyl-thiourea 
• 14269-47-7 N-(3-methyl-4-phenyl-3H-thiazol-2-ylidene)-acetamide 

Relevant academic research and scientific papers

Aqueous NaHSO4 catalyzed regioselective and versatile synthesis of 2-thiazolamines

The green acidic catalyst NaHSO4 was used for the synthesis of some novel substituted 2-thiazolamines in water under mild conditions in high regioselectivity.

Effect of substituents on the regioselectivity of the reaction of α-tosyloxyketones with thioureas in acidic medium: Access to 2-aminothiazoles and 2-imino-2,3-dihydrothiazoles

Regioselective condensation of α-tosyloxyacetophenones 1 and N-substituted thioureas 2 in acidic medium to give regioisomers 2-aminothiazoles I and 2-imino-2,3-dihydrothiazoles II is largely influenced by the substituents present on 1 and 2. A mechanism,

Novel and expedient regioselective synthesis of 2-imino-3-methyl-2,3- dihydrothiazoles

Cyclization of α-tosyloxyacetophenones 1 and N-methylthiourea 2 in acidic medium affords a novel and expedient method to synthesize 2-imino-3-methyl-2,3-dihydrothiazoles 3 with excellent level of regiocontrol. Copyright Taylor & Francis Group, LLC.

The Hantzsch Thiazole Synthesis under Acidic Conditions: Change of Regioselectivity

The condensation of α-halogeno ketones with N-monosubstituted thioureas in neutral solvent leads exclusively to 2-(N-substituted amino)thiazoles.In the present work it was shown that under acidic conditions mixtures of 2-(N-substituted amino)thiazoles and 3-substituted 2-imino-2,3-dihydrothiazoles are formed. (The isomers were distinguished by characteristic differences between their 5-H 1H n.m.r. signals and the i.r.CO bands of their trifluoroacetate derivatives.) The proportions of the 2-imino-2,3-dihydrothiazoles in the mixtures are influenced by experimental features and by the structures of the starting materials.Reactions in 10 M-HCl-EtOH (1:2) at 80 deg C for 20 min were found to be the most efficient for generating 2-imino-2,3-dihydrothiazoles; in the most favourable case 2-imino-3,4-dimethyl-2,3-dihydrothiazole was obtained in 73 percent yield.A possible explanation of the results is discussed.