6149-16-2

Usage

Heterocyclic compound

(It is a compound containing a ring structure with at least one sulfur, oxygen, or nitrogen atom)

Thiazole ring

(A 5-membered ring containing one nitrogen atom and one sulfur atom)

Imine functional group

(A functional group with a nitrogen atom double bonded to a carbon atom)

Reactivity

(2(3H)-Thiazolimine, 3,4-dimethylis highly reactive and can undergo various chemical reactions, such as nucleophilic addition and oxidation)

Key intermediate

(It is a key intermediate in the synthesis of pharmaceuticals and agrochemicals)

Potential applications

(It has potential applications in the fields of medicine and agriculture due to its unique chemical properties and reactivity)

Safety precautions

(It is important to handle 2(3H)-Thiazolimine, 3,4-dimethyl- with care and follow proper safety precautions due to its reactivity and potentially hazardous nature)

Upstream product

• 598-52-7 1-(methyl)-thiourea 
• 78-95-5 chloroacetone 
• 67-64-1 acetone 

Downstream Products

• 15088-00-3 (3,4-dimethyl-3H-thiazol-2-ylidene)-phenyl-thiourea 
• 15090-74-1 N-(5-isopropyl-3,4-dimethyl-3H-thiazol-2-ylidene)-benzamide 
• 15090-78-5 N-(5-isopropyl-3,4-dimethyl-3H-thiazol-2-ylidene)-benzenesulfonamide 
• 15090-79-6 N-(5-isopropyl-3,4-dimethyl-3H-thiazol-2-ylidene)-toluene-4-sulfonamide 
• 15090-81-0 N-(5-tert-butyl-3,4-dimethyl-3H-thiazol-2-ylidene)-benzenesulfonamide 
• 17338-06-6 N-(5-tert-butyl-3,4-dimethyl-3H-thiazol-2-ylidene)-2-hydroxy-benzamide 
• 15090-82-1 N-(5-tert-butyl-3,4-dimethyl-3H-thiazol-2-ylidene)-toluene-4-sulfonamide 
• 15090-77-4 4-chloro-N-(5-isopropyl-3,4-dimethyl-3H-thiazol-2-ylidene)-benzenesulfonamide 
• 15090-72-9 4-amino-N-(5-isopropyl-3,4-dimethyl-3H-thiazol-2-ylidene)-benzenesulfonamide 
• 15090-76-3 N-(5-tert-butyl-3,4-dimethyl-3H-thiazol-2-ylidene)-4-chloro-benzenesulfonamide 
• 15090-80-9 4-acetylamino-N-(5-isopropyl-3,4-dimethyl-3H-thiazol-2-ylidene)-benzenesulfonamide 
• 15090-83-2 4-acetylamino-N-(5-tert-butyl-3,4-dimethyl-3H-thiazol-2-ylidene)-benzenesulfonamide 
• 1276666-76-2 3,4-dimethyl-3H-thiazol-2-ylideneamine(pentafluorophenyl)gold(I) 

Relevant academic research and scientific papers

Condensation of thiourea derivatives with carbonyl compounds: One-pot synthesis of N-alkyl-1, 3-thiazol-2-amines and of 3-alkyl-1, 3-thiazolimines

The reactions of ketones and AT-substituted thioureas, in the presence of HC1 (or HBr) and DMSO afford mixtures of the title compounds which are easily separated on a silica gel column. This method avoids the classical use of a-haloketones. The mechanism of these reactions involves the enolization of ketones and the activation of thiourea sulfur, probably by oxygen transfer from DMSO.

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.