79069-94-6

Usage

InChI:InChI=1/C17H16N2S/c1-3-7-14(8-4-1)11-12-18-17-19-16(13-20-17)15-9-5-2-6-10-15/h1-10,13H,11-12H2,(H,18,19)

Upstream product

• 6815-00-5 N-(2-phenylethyl)thiourea 
• 70-11-1 α-bromoacetophenone 
• 28179-33-1 4-(phenoxy)phenacyl bromide 
• 2257-09-2 Phenethyl isothiocyanate 
• 100-41-4 ethylbenzene 
• 122-78-1 phenylacetaldehyde 
• 2010-06-2 2-Amino-4-phenylthiazole 
• 17336-58-2 4-methyl-N'-(2-phenylethylidene)benzenesulfonohydrazide 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 98-88-4 benzoyl chloride 
• 59795-89-0 phenethyl isocyanide 
• 64-04-0 phenethylamine 
• 5399-30-4 2-oxo-2-phenylethylthiocyanate 

Downstream Products

• 865138-00-7 4-isobutoxy-3-{[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}benzaldehyde 
• 858114-73-5 methyl 4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzoate 

Relevant academic research and scientific papers

Convenient Multicomponent One-Pot Synthesis of 2-Iminothiazolines and 2-Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions

Herein, we present a novel one-pot aqueous reaction for the synthesis of 2-iminothiazolines and 2-aminothiazoles using isocyanides, amines, sulfur, and 2′-bromoacetophenones. The three-component preparation of thioureas is followed by the one-pot cyclization leading to the heterocyclic product. This efficient and mild procedure features excellent step- and atom-economy and enables the chromatography-free preparation of diversely substituted 2-iminothiazoline and 2-aminothiazole derivatives.

Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas

Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(II) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity, providing a facile and efficient approach to access a variety of 2-aminothiazole derivatives with good functional groups tolerance.

Synthetic method for N-alkyl(benzo)thiazole

The invention provides a synthetic method for N-alkyl(benzo)thiazole. The synthetic method comprises the following steps: putting 0.4-0.8 mmol of a carbonyl compound, 0.4-0.8 mmol of p-toluenesulfonylhydrazide and 4-10 mL of a solvent in a flask and carrying out a reaction at 30 DEG C to 80 DEG C for 1 to 3 h; adding 0.4 mmol of 2-aminothiazole, 0.4-0.8 mmol of metal copper salt and 0.4-1.2 mmolof an alkali substance into the above reaction system, carrying out heating to 100 DEG C to 150 DEG C, and continuing the reaction for 2 h to 5 h; terminating the reaction to obtain a reaction productA; and subjecting the product A to purification and impurity separation so as to obtain pure N-alkyl(benzo)thiazole. According to the invention, the intermediate sulfonyl hydrazone is prepared from the carbonyl compound and sulfonyl hydrazide, and reacts with a 2-aminothiazole substance in the presence of a catalyst and under alkali conditions to obtain N-alkyl(benzo)thiazole. The synthetic method of the invention has the advantages of simple operation, low cost, high product yield and wide application range of a substrate. At the same time, the established method can also realize the synthesis of the anti-inflammatory drug fanetizole, and thus has high practical value.

Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles

An efficient and practical C–N bond formation methodology for the synthesis of N-alkylated (benzo)thiazoles was developed, via the copper-catalyzed one-pot two-step reactions of 2-amino(benzo)thiazoles and aldehydes (ketones) with tosylhydrazide. This cross-coupling reaction proceeded smoothly and tolerated a broad range of functional groups (46 examples). A variety of functionalized N-alkylated (benzo)thiazoles were obtained in moderate to high yields. Notably, gram-scale synthesis of fanetizole (anti-inflammatory drug) was also realized through this protocol.

2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas

Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.

Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)

An efficient procedure for the synthesis of 2-aminothiazoles via DBH-mediated oxidative cyclization of styrenes and thioureas is reported. Various alkenes were successfully transformed to the corresponding 2-aminothiazoles in yields of 10–81% via a two-step one-pot manner using DBH as both the bromine source and oxidant. The method can be readily carried out in gram-scale and successfully applied to the synthesis of anti-inflammatory drug fanetizole using styrene as starting material.

A 2-thiocyano HYPNONE derivatives method for the preparation of

The invention discloses a method for preparing 2-sulfur cyano acetophenone derivatives. The method for preparing the 2-sulfur cyano acetophenone derivatives comprises the following steps: dissolving styrene derivatives and ammonium thiocyanate in a solvent, and reacting at 20-30 DEG C to obtain 2-sulfur cyano acetophenone derivatives. According to the method for preparing the 2-sulfur cyano acetophenone derivatives, the styrene derivatives are taken as starting materials; the raw materials are easily available and various in type; products prepared by the method have various in type, can be directly used and can also be used for other further reactions; meanwhile, the method is mild in reaction conditions and simple in reaction operation and post-processing process; an accelerant does not need to be added; the production process meets the green and chemical requirements, is relatively high in yield and is suitable for large-scale production.

Scaling up of continuous flow processes with gases using a tube-in-tube reactor: Inline titrations and fanetizole synthesis with ammonia

The development of a tube-in-tube reactor based on a semipermeable polymer membrane has enabled the efficient transfer of gases into liquid flow streams. In this work we describe the scalability and throughput of this reactor when applied to ammonia gas.

A rapid and high-yielding synthesis of thiazoles and aminothiazoles using tetrabutylammonium salts

A convenient method for the synthesis of thiazoles and aminothiazoles by treatment of phenacyl bromides with thioamides/thiourea in the presence of tetrabutylammonium hexafluorophosphate (Bu4NPF6) at room temperature was developed. The products having high yields were formed rapidly (within 15 min). The method is simple, rapid and practical, generating thiazole derivatives in excellent isolated yields. The structures of the newly synthesized products were identified by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis data. The Japan Institute of Heterocyclic Chemistry.

Catalyst-free efficient synthesis of 2-aminothiazoles in water at ambient temperature

A highly efficient and facile method has been described for the synthesis of substituted 2-aminothiazoles in water without any added catalyst or co-organic solvent. The reaction was carried out at ambient temperature and the products were obtained in excellent isolated yields. The developed protocol is successfully applied for the preparation of an anti-inflammatory drug, fanetizole.