138867-04-6

Basic information

• Product Name: 1H-Imidazole-1-sulfonamide, 5-(2,3-dimethylbenzoyl)-2-[(1,1-dimethylethyl)dimethylsilyl]-N,N-dimethyl -
• CAS NO: 138867-04-6
• Molecular Formula: C20H31N3O3SSi
• Molecular Weight: 421.636
• Mol File: 138867-04-6.mol

Chemical Properties

• CAS DataBase Reference: 1H-Imidazole-1-sulfonamide, 5-(2,3-dimethylbenzoyl)-2-[(1,1-dimethylethyl)dimethylsilyl]-N,N-dimethyl -(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-1-sulfonamide, 5-(2,3-dimethylbenzoyl)-2-[(1,1-dimethylethyl)dimethylsilyl]-N,N-dimethyl -(138867-04-6)
• EPA Substance Registry System: 1H-Imidazole-1-sulfonamide, 5-(2,3-dimethylbenzoyl)-2-[(1,1-dimethylethyl)dimethylsilyl]-N,N-dimethyl -(138867-04-6)

Safety Data

• Hazardous Substances Data: 138867-04-6(Hazardous Substances Data)

Usage

Imidazole ring

A five-membered heterocyclic ring with four carbon atoms and one nitrogen atom, contributing to the compound's aromatic and electronic properties.

Sulfonamide group

A functional group consisting of a sulfur atom double-bonded to an oxygen atom and single-bonded to a nitrogen atom (-SO2NH2), responsible for the compound's reactivity and potential pharmaceutical applications.

Dimethylbenzoyl group

A benzoyl group (a carbonyl group attached to a benzene ring) with two methyl groups attached to the benzene ring, contributing to the compound's lipophilicity and stability.

Dimethylsilyl group

A silicon atom bonded to two methyl groups, providing steric hindrance and affecting the compound's reactivity and solubility.

2,3-dimethyl substitution

The presence of two methyl groups on the benzene ring at positions 2 and 3, which can influence the compound's electronic properties and steric effects.

Complex chemical structure

The combination of various functional groups and substituents, making the compound a potential candidate for diverse applications in fields such as pharmaceuticals, material science, and organic synthesis.

Upstream product

• 21900-46-9 2,3-dimethylbenzoyl chloride 
• 78162-58-0 N,N-dimethyl-1H-imidazole-1-sulfonamide 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 86347-14-0 medetomidine 
• 86347-14-0 (+/-)-4(5)-<1-(2,3-Dimethylphenyl)ethyl-1H-imidazole> 
• 91874-85-0 (2,3-dimethylphenyl)(1H-imidazol-4-yl)methanone 

Relevant articles and documents

Method for synthesizing dexmedetomidine hydrochloride

The invention belongs to the technical field of drug preparation, and particularly relates to a method for synthesizing dexmedetomidine hydrochloride. The method for synthesizing dexmedetomidine hydrochloride comprises the steps that reaction of 2,3-dimethylbenzoyl chloride and 1-N,N-dimethyl sulfonyl-2-(tert-butyldimethylsily)-5-(2,3-dimethyl benzoyl) imidazole is adopted, reflux is carried out to remove a protecting group under the action of hydrochloric acid, intermediate 4(5)-(2,3-dimethyl benzoyl) imidazole is obtained, lastly, reduction is carried out to obtain medetomidine under the action of monomethylamine, dexmedetomidine is obtained through the resolution of medetomidine under the action of tartaric acid, and lastly, dexmedetomidine is salified with hydrochloric acid to obtain dexmedetomidine hydrochloride. Compared with the prior art, the method for synthesizing dexmedetomidine hydrochloride has the advantages that a synthetic route is shorter, the operation is easy, and astarting material is easy to obtain.

Expedient synthesis of 4(5)-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole, the α2-adrenergic agonist medetomidine

(+)-4(5)-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole hydrochloride (5) is prepared in three steps in 79% overall yield from 1-(N,N-dimethylsulfamoyl)imidazole by bis-protection, regioselective lithiation followed by an efficient tandem addition-reduction of the resulting 2,3-dimethylbenzoyl chloride adduct with lithium/ammonia/ammonium chloride.