20980-00-1

Upstream product

• 103-88-8 4-bromoacetanilide 
• 861797-02-6 N-(4-bromo-phenyl)-3-thio-malonamic acid 
• 59862-55-4 p-bromoacetophenone oxime 
• 98-09-9 benzenesulfonyl chloride 
• 75-36-5 acetyl chloride 
• 106-40-1 4-bromo-aniline 
• 861795-98-4 ethyl 2-((4-bromophenyl)carbamothioyl)-3-oxobutanoate 
• 1985-12-2 4-Bromophenyl isothiocyanate 
• 917-54-4 methyllithium 
• 59862-55-4 (E)-1-(4-bromophenyl)ethan-1-one oxime 

Downstream Products

• 5304-21-2 6-bromo-2-methylbenzothiazole 
• 98437-33-3 1-(4'-bromophenyl)-5-methyl-1H-tetrazole 
• 103-88-8 4-bromoacetanilide 

Relevant academic research and scientific papers

Dehydrative Beckmann rearrangement and the following cascade reactions

The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.

A Robust, Eco-Friendly Access to Secondary Thioamides through the Addition of Organolithium Reagents to Isothiocyanates in Cyclopentyl Methyl Ether (CPME)

The nucleophilic addition of widely available and variously functionalized organolithium reagents to isothiocyanates represents a straightforward, high-yielding, one-pot method to access secondary thioamides. The simple reaction conditions required and the broad scope (>50 cases examples) makes it a robust and reliable method to access both simple and complex thioamides, including enantiopure ones. Noxious and unpleasant-smelling sulfurating agents, usually employed in the literature established methods, are avoided during the whole synthetic procedure thus, rendering the protocol highly attractive, also for sustainability aspects.

Facile synthesis of thioamides via P2S5-mediated beckmann rearrangement of oximes

A facile and efficient approach to the synthesis of secondary thioamides from ketoximes via Beckmann rearrangement has been established, using phosphorus pentasulfide as a dehydrating and thiating agent. It is also efficient for the preparation of primary thiobenzamide from benzaldoxime. This approach features simple-operation, easy-control and good to excellent yields.