33142-18-6

Usage

Uses

Used in Pharmaceutical Synthesis:
N-Phenyl-2-aminothiazole is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity make it a preferred building block for the development of new drugs with potential therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, N-Phenyl-2-aminothiazole serves as a crucial component in the production of pesticides and other crop protection agents. Its incorporation enhances the effectiveness of these chemicals, contributing to improved agricultural yields and pest control.
Used in Organic Reactions:
N-Phenyl-2-aminothiazole is utilized as a versatile building block in a wide range of organic reactions. Its ability to participate in various chemical transformations makes it an indispensable tool for organic chemists, facilitating the synthesis of complex organic molecules.
Used in Therapeutic Research:
N-Phenyl-2-aminothiazole has been studied for its potential therapeutic properties, including its role in treating certain medical conditions. Its unique chemical structure and reactivity make it a promising candidate for the development of novel therapeutic agents.

InChI:InChI=1/C9H8N2S/c1-2-4-8(5-3-1)11-9-10-6-7-12-9/h1-7H,(H,10,11)

Upstream product

• 133972-63-1 2-phenylaminothiazole-5-carboxylic acid 
• 7647-01-0 hydrogenchloride 
• 96-50-4 2-thiazolylamine 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 103-85-5 monophenylthiourea 
• 3034-52-4 2-chlorothiazole 
• 62-53-3 aniline 
• 76510-73-1 C₅H₈ClNOS 
• 3034-53-5 2-bromo-1,3-thiazole 
• 75-07-0 acetaldehyde 
• 621-62-5 chloroacetaldehyde diethyl acetal 
• 10140-87-1 1,2-dichloroethyl acetate 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 

Downstream Products

• 63615-95-2 5-Bromo-2-(N-phenylamino)thiazole 
• 840493-92-7 N-phenyl-N-(thiazol-2-yl)carbamic acid 1,1-dimethylethyl ester 
• 840493-89-2 2,2-dimethyl-N-phenyl-N-(thiazol-2-yl)propanamide 
• 63616-01-3 phenyl-((3ar,7at)-3a,5,6,7a-tetrahydro-[1,4]dioxino[2,3-d]thiazol-2-yl)-amine 
• 63616-01-3 phenyl-((3ar,7ac)-3a,5,6,7a-tetrahydro-[1,4]dioxino[2,3-d]thiazol-2-yl)-amine 
• 1290104-92-5 C₂₀H₁₆N₂S₂ 
• 1290104-86-7 C₂₂H₁₇N₃O₂S 
• 1290104-80-1 N-benzyl-N,5-diphenylthiazol-2-amine 
• 1290104-85-6 C₂₂H₁₇N₃O₂S 
• 1290104-83-4 C₂₃H₂₀N₂S 
• 1290104-88-9 C₂₂H₁₇FN₂S 
• 1290104-84-5 C₂₃H₂₀N₂S 
• 1290104-87-8 C₂₃H₂₀N₂OS 
• 1290104-82-3 C₂₅H₂₂N₂O₂S 

Relevant academic research and scientific papers

PROSTACYCLIN RECEPTOR AGONIST

A compound represented by formula (I) or an isomer or a pharmaceutically acceptable salt thereof. The present invention also relates to an application of the same in preparing a drug for treating a disease related to a PGI2 receptor.

Molecular docking and glucosidase inhibition studies of novel N-arylthiazole-2-amines and Ethyl 2-[aryl(thiazol-2-yl)amino]acetates

This study describes an efficient synthesis of a series of novel ethyl 2-[aryl(thiazol-2-yl)amino]acetates (4a–l) from N-arylthiazole-2-amines (3a–l). The reaction conditions were optimized and the best results were obtained when ethyl chloroacetate was used as alkylating agent and NaH as base in THF. α-glucosidase and β-glucosidase inhibition activities of N-arylthiazole-2-amines (3a–l) and ethyl 2-[aryl(thiazol-2-yl)amino]acetates (4a–l) were determined, which revealed that most of the compounds showed high percentage inhibition towards the enzymes. Among the synthesized compounds, 4e appeared to have the highest inhibition towards α-glucosidase having IC50 value of 150.4 ± 1.9 μM which was almost two folds as compared to acarbose (336.9 ± 9.0 μM) taken as standard. Molecular docking of the compounds 3g, 3f, 4a, and 4e was also performed which showed their bonding modes to the enzyme’s active sites via amino and acetate groups, respectively.

Synthesis, characterization and density functional theory study of some new 2-anilinothiazoles

We report here a comparative theoretical and experimental study of anilinothiazoles. The anilinothiazoles are synthesized by acid catalyzed condensation of N-phenylthioureas and 2-chloro-1,1-dimethoxyethane. Substituted anilines were employed to introduce substitution in 2-anilinothiazoles. The experimental geometric and spectroscopic properties of the anilinothiazoles are compared with the theoretically calculated ones. The model developed here comprises of geometry optimization at B3LYP method of DFT at 6-31+G(d) basis set. The optimized geometric parameters of anilinothiazoles show nice correlations with values obtained from X-ray crystal structure. Differences of up to 0.02 ? in bond length and 1.0° in bond angles are observed except SC2N6 and C7N6C2 where this difference is 1.77°and 6.01°, respectively. The vibrational spectra are calibrated with a common scaling factor of 0.9613 and show nice correlations with the experimental IR spectra. The UV-Vis spectra calculated at 190-450 nm range show 20-25 nm difference from the experimental spectra. The consistent difference may be attributed to the condensed phase nature of anilinothiazoles however the theoretical spectra are for single molecules. In addition HOMO, LUMO and the associated band gaps are also calculated and depicted.

Convenient and reliable routes towards 2-aminothiazoles: Palladium-catalyzed versus copper-catalyzed aminations of halothiazoles

Two efficient methods for the amination of 2-halothiazoles are presented here. A first protocol requires a Pd/L system. Several 2-aminothiazoles were synthesized under optimized conditions and isolated in good yields. The first palladium-catalyzed C-N coupling reactions between 2-halothiazoles and primary alkylamines are presented. In a second part, ligand-free copper-catalyzed aminations of 2-halothiazoles by alkylamines and aniline in a green solvent have been developed. The protocol is very effective for primary and secondary amines and perfectly tolerates the presence of another halide moiety on the 2-halothiazole. The reaction occurs under the assistance of microwave irradiation, which drastically decreases the reaction time. The reaction leads to the formation of 2-aminothiazoles, key molecules in pharmaceutical research. Copyright

Synthesis of 5-arylated N-arylthiazole-2-amines as potential skeletal muscle cell differentiation promoters

A series of N-arylthiazole-2-amines was prepared and their biological activity for the promotion of skeletal muscle cell differentiation was investigated, a process of significant importance in muscle regeneration. A versatile new synthetic route towards

Polyarylated thiazoles via a combined halogen dance - Cross-coupling strategy

The application of the halogen dance reaction for the synthesis of starting materials for cross-coupling reactions is reported. The obtained compounds were then successfully applied, in sequential Stille and Suzuki-Miyaura cross-coupling reactions to obta

Optimization of the conditions for copper-mediated N-arylation of heteroarylamines

Simple and inexpensive copper-mediated N-arylation of heteroarylamines was achieved by using N,N′-dimethylethylenediamine as a ligand and K 2CO3 as a base in dioxane heated at 100°C. In this coupling reaction, the influence of the copper species, ligand, base and solvent was investigated in detail. N-Arylated derivatives of several heteroarylamines were synthesized under optimized reaction conditions, and all the products were isolated in good yields. By controlling the amount of CuI/DMEDA added, heteroarylamines with weak nucleophilic activity were coupled with aryl iodides or aryl bromides. The activity of the copper catalyst for this C-N bond-forming reaction follows the order CuI > Cu0 > Cu II. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Reactivity of 2-aminothiazole and 2- or 6-aminobenzothiazole derivatives towards the triphenylbismuth diacetate/catalytic copper diacetate phenylation system

The copper diacetate catalysed reaction of triphenylbismuth diacetate with 6-aminobenzothiazole compounds afforded selectively the 6-phenylamino derivatives in good to high yields. A similar reaction with 2-aminothiazole or 2-amino-benzothiazole compounds gave mixtures of the monophenylated and diphenylated products 2-phenylaminothiazole and 2-(N-phenylamino)-3-N′- phenylthiazole derivatives, respectively, with the diphenyl product being predominant. Semi-empirical calculations with the SAM1/D and CHAIN methods performed on the evolution of a 2-aminobenzothiazole - copper(III) intermediate were in good qualitative agreement with the experimental results. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Studies on Decarboxylation Reactions. Part 7. Kinetic Study of the Decarboxylation of 2-Amino- and 2-Phenylamino-thiazole-5-carboxylic Acids

The rate constants of the decarboxylation reaction of 2-amino- and 2-phenylamino-thiazole-5-carboxylic acid (3a-b), and, for comparison, of 5-phenylamino-1,3,4-thiadiazole-2-carboxylic acid (2b) have been measured in water over a range of proton activities.The results obtained suggest: (i) compound 2b decarboxylates, in the whole range of proton activity studied, through a unimolecular decarboxyprotonation mechanism characteristic of 1,3,4-oxa- and 1,3,4-thiadiazole derivatives; (ii) in contrast, 3a-b decarboxylate via either a unimolecular decarboxyprotonation or a bimolecular protiodecarboxylation mechanism as a function of proton activity.