3829-80-9

Usage

Uses

1. Used in Research Chemistry:
Methyl 2-amino-4-methylthiazole-5-carboxylate is used as a research chemical for various scientific investigations. Its unique structure and properties make it a valuable compound for exploring new chemical reactions, synthesizing novel molecules, and understanding the underlying mechanisms of certain chemical processes.
2. Used in Pharmaceutical Development:
In the pharmaceutical industry, Methyl 2-amino-4-methylthiazole-5-carboxylate can be utilized as a key intermediate or building block in the synthesis of new drugs. Its chemical properties may contribute to the development of innovative therapeutic agents with potential applications in treating various diseases and medical conditions.
3. Used in Material Science:
Methyl 2-amino-4-methylthiazole-5-carboxylate may also find applications in material science, where its unique properties can be exploited to create new materials with specific characteristics. These materials could have potential uses in various industries, such as electronics, aerospace, or automotive, depending on their properties.
4. Used in Analytical Chemistry:
Methyl 2-amino-4-methylthiazole-5-carboxylate can be employed as a reference compound or standard in analytical chemistry. It can be used to calibrate instruments, validate analytical methods, or serve as a control in experiments, ensuring the accuracy and reliability of the results obtained.

InChI:InChI=1/C6H8N2O2S/c1-3-4(5(9)10-2)11-6(7)8-3/h1-2H3,(H2,7,8)

Upstream product

• 4755-81-1 methyl 2-chloroacetoacetate 
• 17356-08-0 thiourea 
• 3952-66-7 methyl 2-oxobutanoate 
• 3600-18-8 ethyl α-bromoacetoacetate 
• 21731-17-9 methyl 3-aminocrotonate 
• 247242-38-2 (E)-3-amino-2-thiocyanatobut-2-enoic acid methyl ester 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 1048364-00-6 methyl 2-(bis(4-acetylbenzyl)amino)-4-methylthiazole-5-carboxylate 
• 1048364-04-0 methyl 2-(N-(4-acetylbenzyl)acetamido)-4-methylthiazole-5-carboxylate 
• 1048363-72-9 methyl 2-(3-(4-acetylphenyl)ureido)-4-methylthiazole-5-carboxylate 
• 81569-44-0 methyl 4-methyl thiazole-5-carboxylate 
• 380577-04-8 C₂₂H₁₈N₂O₆S₂ 
• 6122-01-6 2-[(N-benzyl-N-phenyl-glycyl)-amino]-4-methyl-thiazole-5-carboxylic acid methyl ester 
• 6802-40-0 2-[(N-ethyl-N-phenyl-glycyl)-amino]-4-methyl-thiazole-5-carboxylic acid methyl ester 
• 6746-17-4 4-methyl-2-[(N-methyl-N-phenyl-glycyl)-amino]-thiazole-5-carboxylic acid methyl ester 
• 433253-78-2 C₂₄H₂₀N₂O₆S 
• 371922-20-2 C₂₃H₁₇ClN₂O₅S 
• 371225-96-6 C₂₃H₁₈N₂O₅S 
• 385393-26-0 C₂₃H₂₀N₂O₆S₂ 

Relevant academic research and scientific papers

1-Methylimidazolium ionic liquid supported on Ni@zeolite-Y: fabrication and performance as a novel multi-functional nanocatalyst for one-pot synthesis of 2-aminothiazoles and 2-aryl benzimidazoles

In the present study, 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride-supported Ni@zeolite-Y-based nanoporous materials (Ni@zeolite-Im-IL) were synthesized and their structures were confirmed using different characterization techniques such as FT-IR, FE-SEM, EDX, XRD, BET and TGA-DTG analyses. In order to synthesize this multi-functional nano-system, zeolite-NaY was modified first, with exchanged Ni2+ ions and 3-chloropropyltriethoxysilane (CPTES) as a coupling reagent and then functionalized to imidazolium chloride ionic liquid by N-methylimidazole. New multi-functional nano-material of Ni@zeolite-Im-IL demonstrated high activity in the catalytic synthesis of 2-aminothiazoles 3a–l by one-pot reaction of methylcarbonyls, thiourea and iodine at 80?°C in DMSO with good to excellent yields (85–98%). Also, the catalytic synthesis of 2-aryl benzimidazoles, 6a–m was performed by the condensational reaction of o-arylendiamine and aromatic aldehydes in EtOH at room temperature with excellent yields (90–98%). Advantages of this efficient synthetic strategy include higher purity and shorter reaction time, excellent yield, easy isolation of products, the good stability, activity and feasible reusability of the metallic ionic liquid nanocatalyst. These benefits have made this method more compatible with the principles of green chemistry. Graphical abstract: [Figure not available: see fulltext.]

Asparagine functionalized Al2O3 nanoparticle as a superior heterogeneous organocatalyst in the synthesis of 2-aminothiazoles

Asparagine functionalized aluminum oxide nanoparticles (Asp-Al2O3) have been prepared by a two-step procedure involving the grafting of Al2O3 with 3-chloropropyltrimethoxysilane (CPTMS) and subsequent organofunctionalization using asparagine amino acid. It is shown that Asp-Al2O3 exhibits as an active nanocatalyst for the preparation of 2-aminothiazoles is achieved by one-pot reaction of methylcarbonyls, thiourea and iodine. The structure of Asp-Al2O3 was characterized by fourier transform infrared radiation (FT-TR), thermal gravimetric analysis (TGA), X-ray diffraction (XRD), scanning electron microscopic (SEM), and energy-dispersive analysis of X-ray (EDAX) analyses. Advantages of this modified methodology include higher purity and excellent yield of products, greener and cleaner conditions, easy isolation of products and convenient manipulation. Moreover, immobilization of organocatalysts on the Al2O3 surface are stable under the catalytic reaction conditions resulting their efficient reuse.

Visible Light-Mediated Coupling of Thioureas and 1,3-Dicarbonyls: Towards a Leaving Group-Free Synthesis of Aminothiazoles

A synthesis of aminothiazoles from various 1,3-dicarbonyls and thioureas without a leaving group has been developed. The reaction is photocatalyzed by tetraiodofluorescein, an organic dye. Under irradiation with green LEDs, a sulfur radical is generated in situ from thiourea, followed by addition to the enol tautomer, forming the aminothiazole backbone. This novel strategy provides a greener alternative to the traditional leaving group protocols, with excellent atom economy. (Figure presented.).

TBHP/AIBN-Mediated Synthesis of 2-Amino-thioazoles from Active Methylene Ketones and Thiourea under Metal-free Conditions

A new oxidative system of tert-butyl hydroperoxide (TBHP)/azodiisobutyronitrile (AIBN) has been used for the first time for a convenient, metal-free synthesis of substituted 2-aminothioazoles from active methylene ketone derivatives and thiourea. The reaction is postulated to proceed via an oxidative cyclization initiated by a radical process and followed by a condensation reaction.

Method for synthesizing 2-aminothiazole derivative

The invention discloses a method for synthesizing a 2-aminothiazole derivative. The method comprises the following steps: by taking a ketone derivative (I) with an electron withdrawing group at the alpha position and thiourea (II) as raw materials, t-buty

Nanostarch: a novel and green catalyst for synthesis of 2-aminothiazoles

Abstract: In this work, starch nanoparticles as a green and cheap catalyst were obtained based on the precipitation of amorphous starch in ethanol. It was found that starch nanoparticles are efficient catalyst for the synthesis of 2-aminothiazoles using methylcarbonyl compounds and thiourea as precursors. The use of green and biodegradable nanostarch makes this present methodology quite simple, shorter reaction times and milder conditions, and more convenient and economically viable compared to catalyzed methods reported in the literature. Graphical abstract: [Figure not available: see fulltext.]

C[sbnd]N bond formation in alicyclic and heterocyclic compounds by amine-modified nanoclay

In the current protocol, amine functionalized montmorillonite K10 nanoclay (NH2-MMT) was applied to catalyze the formation of C[sbnd]N bonds in the synthesis of azines and 2-aminothiazoles at room temperature. In comparison with the current methods of C[sbnd]N bond formation, this approach displays specific advantages include atom economy, clean conversion, design for energy efficiency, the use of nontoxic and heterogeneous catalyst, higher purity and yields, safer solvent and reagents for this organic transformation.

Synthesis of 2-aminothiazoles from methylcarbonyl compounds using a Fe3O4 nanoparticle-: N -halo reagent catalytic system

An efficient protocol is developed for the synthesis of 2-aminothiazoles from unfunctionalized methylcarbonyl compounds using Fe3O4 nanoparticle-N-halo reagent catalytic systems. 1,3-dichloro-5,5-dimethylhydantoin (DCDMH), N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) as N-halo reagents were explored and the best results were obtained for DCDMH. Fe3O4 nanoparticle-DCDMH as an active, reusable, excellent, highly stable magnetic catalyst was used in this process. Advantages of this efficient method include greener and cleaner conditions, shorter reaction time, excellent yield of products, easy separation using a simple external magnetic field, low cost and operational simplicity.

Montmorillonite K10: an effective catalyst for synthesis of 2-aminothiazoles

An efficient one-pot synthesis of 2-aminothiazoles from methylcarbonyl and thiourea has been developed using montmorillonite-K10 as a catalyst at 80?°C in DMSO medium. A plausible mechanism is proposed in which α-iodomethylcarbonyls are formed via methylcarbonyls as raw material using iodine as iodination reagent.

Magnetic carbon nanotube-supported imidazolium cation-based ionic liquid as a highly stable nanocatalyst for the synthesis of 2-aminothiazoles

Magnetic carbon nanotube-supported imidazolium ionic liquid (CNT-Fe3O4-IL) was synthesized and investigated using various characterization techniques, including Fourier transform infrared and Raman spectroscopies, X-ray diffraction, vibrating sample magnetometry, scanning and transmission electron microscopies, and thermogravimetric and differential thermal analyses. In order to synthesize the CNT-Fe3O4-IL nanocomposites, Fe3O4-decorated multi-walled CNTs were modified with 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride. This catalytic system was found to be a highly stable, active, reusable and solid-phase catalyst for the synthesis of 2-aminothiazoles via the one-pot reaction of ketone, thiourea and N-bromosuccinimide under mild conditions. Immobilized magnetic ionic liquid catalysis combines the advantages of ionic liquid media with magnetic solid support nanomaterials which enables the application of nanotechnology and green chemistry in chemical processes. Copyright