110960-33-3

Basic information

• Product Name: 4-(4-fluorophenyl)-2-imino-3-methyl-2,3-dihydrothiazole
• Synonyms: 4-(4-fluorophenyl)-2-imino-3-methyl-2,3-dihydrothiazole
• CAS NO: 110960-33-3
• Molecular Weight: 208.259
• Mol File: 110960-33-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-(4-fluorophenyl)-2-imino-3-methyl-2,3-dihydrothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-fluorophenyl)-2-imino-3-methyl-2,3-dihydrothiazole(110960-33-3)
• EPA Substance Registry System: 4-(4-fluorophenyl)-2-imino-3-methyl-2,3-dihydrothiazole(110960-33-3)

Safety Data

• Hazardous Substances Data: 110960-33-3(Hazardous Substances Data)

Upstream product

• 598-52-7 1-(methyl)-thiourea 
• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 357952-79-5 1-(4-fluorophenyl)-2-(p-tolylsulfonyloxy)ethanone 
• 456-04-2 2-Chloro-4'-fluoroacetophenone 

Downstream Products

• 110960-35-5 4-(4-fluorophenyl)-3-methyl-2-trifluoroacetylimino-2,3-dihydrothiazole 

Relevant articles and documents

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.