5036-02-2

Basic information

• Product Name: tetramisole
• Synonyms: (+-)-2,3,5,6-tetrahydro-6-phenylimidazo(2,1-b)thiazole;DL-tetramisole;Imidazo2,1-bthiazole, 2,3,5,6-tetrahydro-6-phenyl-;Tetramizole;6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole;6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole
• CAS NO: 5036-02-2
• Molecular Formula: C₁₁H₁₂N₂S
• Molecular Weight: 204.29138
• EINECS: 225-729-3
• Mol File: 5036-02-2.mol

Chemical Properties

• Melting Point: 87-89°
• Boiling Point: 344.4 °C at 760 mmHg
• Flash Point: 162.1 °C
• Appearance: /
• Density: 1.32 g/cm³
• Storage Temp.: 2-8°C
• Solubility: DMSO; Methanol
• PKA: 10.00±0.40(Predicted)
• CAS DataBase Reference: tetramisole(CAS DataBase Reference)
• NIST Chemistry Reference: tetramisole(5036-02-2)
• EPA Substance Registry System: tetramisole(5036-02-2)

Safety Data

• Hazardous Substances Data: 5036-02-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tetramisol is used as an intermediate in the synthesis of H595270, which is a metabolite of the anthelmintic Tetramisole. This application is significant because it contributes to the development of medications that can effectively treat parasitic worm infections, improving the health and well-being of individuals affected by these parasites.
Additionally, given its role in the synthesis of a metabolite of an anthelmintic, Tetramisol may also have potential applications in research and development within the pharmaceutical industry. This could include further exploration of its properties, potential interactions with other compounds, and possible uses in the creation of new drugs or therapies.

InChI:InChI=1/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2

Upstream product

• 3882-98-2 2-amino-4,5-dihydrothiazole hydrochloride 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 17356-08-0 thiourea 
• 5086-74-8 tetramisole hydrochloride 
• 15643-70-6 [3-(2-chloro-2-phenyl-ethyl)-thiazolidin-2-ylidene]-amine; hydrochloride 
• 69510-65-2 1-(2-hydroxy-ethyl)-4-phenyl-imidazolidine-2-thione 
• 36986-90-0 2-[2-(2-hydroxy-2-phenyl-ethylamino)-ethyl]-isothiourea 
• 70-11-1 α-bromoacetophenone 
• 4335-26-6 2-(2-imino-thiazolidin-3-yl)-1-phenyl-ethanone; hydrobromide 
• 10060-88-5 2-imino-3-(2-hydroxy-2-phenylethyl)thiazolidine 

Downstream Products

• 87047-19-6 D,L-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]-thiazolium 4-cyano-2-iodo-6-nitrophenoxide 
• 65172-55-6 7-(methylsulfanyl-phenylimino-methyl)-6-phenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazolium; iodide 
• 64892-34-8 benzyl-(1-phenyl-2-thiazolidin-3-yl-ethyl)-amine 
• 14769-73-4 Levamisole 
• 14769-74-5 R-(+)-6-phenyl-2,3,5,6-tetrahydro-imidazo<2,1b>thiazole 
• 16595-80-5 levamisole hydrochloride 
• 16595-76-9 (+)-Tetramisole hydrochloride 
• 66235-01-6 6-(4-nitro-phenyl)-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazole 
• 65172-61-4 1,3-dimethyl-6-phenyl-tetrahydro-thiazolo[2',3':2,3]imidazo[1,2-a][1,3,5]triazine-2,4-dione 
• 65172-53-4 7-[(3,4-dichloro-phenyl)-thiocarbamoyl]-6-phenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazolium betaine 
• 65172-58-9 1,3,6-triphenyl-tetrahydro-thiazolo[2',3':2,3]imidazo[1,2-a][1,3,5]triazine-2,4-dione 
• 65172-56-7 6-phenyl-7-(toluene-4-sulfonylcarbamoyl)-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazolium betaine 
• 65172-59-0 1,3-bis-(4-chloro-phenyl)-6-phenyl-tetrahydro-thiazolo[2',3':2,3]imidazo[1,2-a][1,3,5]triazine-2,4-dione 

Relevant articles and documents

Preparation method of tetraimidazole hydrochloride

The invention provides a preparation method of tetraimidazole hydrochloride, which comprises the following steps: preparing tetraimidazole; the preparation method comprises the following step: reacting tetraimidazole, 1, 2-dibromoethyl benzene and 2-aminothiazoline hydrochloride to generate tetraimidazole. The synthetic route is shorter, the comprehensive yield is higher than that of other processroutes, styrene is used as an initiator, tetra-imidazole free alkali is used as a final product, the yield of the hydroxysalt process route is about 65%, the yield of the N (2chloroethyl) alpha (chloromethyl) benzylamine hydrochloride process route is about 72%, and the yield can reach 85% or above when the patent route is used. Meanwhile, the problem of large amount of waste water and waste saltgenerated by multi-step reactions such as chlorination, hydrolysis and cyclization is avoided, the investment of reaction equipment such as an autoclave is avoided, the green chemical engineering requirement is met, the economic benefit is remarkable, and the industrial prospect is good.

Preparation method of tetraimidazole free alkali

The invention discloses a preparation method of tetraimidazole free alkali. Alpha-[[(2-hydroxyethyl)amino]methyl]benzyl alcohol reacts with thionyl chloride, then water is added for heating dissolution, after activated carbon thermal filtration, N-(2-chloroethyl)-alpha-(chloromethyl)-benzylamine hydrochloride is obtained through cooling crystallization, then N-(2-chloroethyl)-alpha-(chloromethyl)-benzylamine hydrochloride and thiourea are subjected to direct cyclization, and tetraimidazole free alkali is generated. The method is simple in production process, mild in reaction condition and highin total yield, the production cost is reduced, the generation amount of three wastes is small, the double contradiction between economy and environment in the development process of modern enterprises is well solved, and the production process has great competitiveness and good industrial prospects.

Total Synthesis of (+)-Granatumine A and Related Bislactone Limonoid Alkaloids via a Pyran to Pyridine Interconversion

We report the first total synthesis of (+)-granatumine A, a limonoid alkaloid with PTP1B inhibitory activity, in ten steps. Over the course of this study, two key methodological advances were made: a cost-effective procedure for ketone α,β-dehydrogenation using allyl-Pd catalysis, and a Pd-catalyzed protocol to convert epoxyketones to 1,3-diketones. The central tetrasubstituted pyridine is formed by a convergent Knoevenagel condensation and carbonyl-selective electrocyclization cascade, which was followed by a direct transformation of a 2H-pyran to a pyridine. These studies have led to the structural revision of two members of this family.

DIHYDRO-5,6 IMIDAZOTHIAZOLES, DIHYDRO-2,3 IMIDAZOBENZOTHIAZOLES, ANALOGUES DU LEVAMISOLE

New compounds containing 5,6-dihydro imidazothiazole 2,3,5,6-tetrahydro imidazothiazole and 2,3-dihydro imidazobenzothiazole rings, substituted by heterocycles analogue to chromones, were synthesized and screened against three nematodes, in vitro.The results indicate moderate anthelmintic properties, compared to levamisole; nevertheless, some products exhibit a significant degree of activity.

Processes for the preparation of tetramisole

Processes for reacting arylvinyl oxides and alkoxyethylamines to provide novel N-substituted alkoxyethylamines; processes for reacting the novel N-substituted amines with nitriles to provide novel amidoamines; processes for preparing novel diamines from the amidoamines, together with the novel nitrogen-containing products so produced, such products being useful for the preparation of various imidazothiazoles including tetramisole.

Method for racemissing d (or l) tetramisole, and the relative product

D-tetramisole, or its l-tetramisole enantiomer, is racemized in solution in dimethylsulphoxide in the presence of a catalytically effective amount of potassium hydroxide.

Intermediates for synthesis of tetramisole, levamisole and their derivatives

A process for the manufacture of 1-(2-alkoxyethyl)-4-phenyl-4-imidazolin-2-ones, 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones, 1-(2-alkoxyethyl)-4-phenyl-imidazolidine-2-thiones, certain of the corresponding 1-(2-hydroxyethyl) derivatives and their 3-acylated derivatives, and certain related compounds which are all useful as intermediates in a new process for the manufacture of tetramisole, dl-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazole, and its derivatives. The compound tetramisole is useful as an anthelmintic.

Process for preparing 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

This disclosure relates to a process for the manufacture of compounds of the formula STR1 which comprises ring-closing a compound of the formula STR2 wherein the variables are as defined infra.