14769-74-5

Basic information

• Product Name: dexamisole
• Synonyms: dexamisole;(6R)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole;(6R)-6β-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole
• CAS NO: 14769-74-5
• Molecular Formula: C₁₁H₁₂N₂S
• Molecular Weight: 204.29
• EINECS: 238-837-0
• Mol File: 14769-74-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 344.4°Cat760mmHg
• Flash Point: 162.1°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 6.61E-05mmHg at 25°C
• Refractive Index: 1.712
• PKA: 10.00±0.40(Predicted)
• CAS DataBase Reference: dexamisole(CAS DataBase Reference)
• NIST Chemistry Reference: dexamisole(14769-74-5)
• EPA Substance Registry System: dexamisole(14769-74-5)

Safety Data

• Hazardous Substances Data: 14769-74-5(Hazardous Substances Data)

Usage

Uses

Antidepressant.

Definition

ChEBI: A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole that has R configuration.

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/t10-/m0/s1

Upstream product

• 5086-74-8 tetramisole hydrochloride 
• 5036-02-2 Tetramisole 

Relevant articles and documents

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.

Effect of achiral support on the resolution of tetramisole by supercritical fluid extraction

The enantiomers of tetramisole were produced by partial diastereomeric salt formation with O,O′-dibenzoyl-(2R,3R)-tartaric acid monohydrate and subsequent supercritical fluid extraction (SFE) of the unreacted enantiomers in the presence of an achiral support. The effect of the activated carbon and Perfil 100 on the efficiency of chiral separation were studied. The kinetics of the process was found to be an important factor affecting enantioselectivity. When the parameters were properly set, much better resolution efficiency (F) and higher enantiomeric purity were achieved than in the equilibrium. The presence of Perfil 100 and activated carbon caused an increase as high as 53 and 84% in F, respectively, compared to that achieved without using any supporting material. Thus during the development of a resolution procedure, beside the proper resolution agent, optimised molar ratio and other parameters, the selection of achiral addict(s) may be also an important point.

A CONVENIENT METHOD FOR OPTICAL RESOLUTIONS VIA DIASTEREOISOMERIC SALT FORMATION

With the advantage of the method using two immiscible solvents and half-equivalent amount of the resolving agent, higher optical purity can be obtained than in cases of any other resolution via diastereoisomeric salt formation, besides it is a faster procedure for resolution of a new racemate as well.