147372-41-6Relevant articles and documents
Development of a continuous process for α-thio-β-chloroacrylamide synthesis with enhanced control of a cascade transformation
Dennehy, Olga C.,Cacheux, Valérie M. Y.,Deadman, Benjamin J.,Lynch, Denis,Collins, Stuart G.,Moynihan, Humphrey A.,Maguire, Anita R.
, p. 2511 - 2522 (2016)
A continuous process strategy has been developed for the preparation of α-thio-β-chloroacrylamides, a class of highly versatile synthetic intermediates. Flow platforms to generate the α-chloroamide and α-thioamide precursors were successfully adopted, progressing from the previously employed batch chemistry, and in both instances afford a readily scalable methodology. The implementation of the key α-thio-β-chloroacrylamide casade as a continuous flow reaction on a multi-gram scale is described, while the tuneable nature of the cascade, facilitated by continuous processing, is highlighted by selective generation of established intermediates and byproducts.
Regioselective Thermal [3+2]-Dipolar Cycloadditions of α-Diazoacetates with α-Sulfenyl/Sulfinyl/Sulfonyl-β-Chloroacrylamide Derivatives to Form Densely Functionalised Pyrazoles
Flynn, Aaran J.,Ford, Alan,Khandavilli, U. B. Rao,Lawrence, Simon E.,Maguire, Anita R.
supporting information, p. 5368 - 5384 (2019/06/24)
Highly regioselective synthetic methodology leading to densely functionalised C(3), C(4) and C(5) substituted pyrazoles 10a–q, 14a-i and 16a–g via thermal [3+2]-dipolar cycloaddition, of α-diazoacetates and α-thio-β-chloroacrylamides, at the sulfide, sulfoxide and sulfone levels of oxidation, is described. This method allows access to C(4)-sulfenyl or sulfonyl pyrazoles, through migration of the sulfur substituent at the sulfide and sulfone oxidation levels, while elimination of the sulfinyl group leading to 3,5-disubstituted pyrazoles, is observed. While the sulfide migration is readily rationalised, the carbon to carbon 1,2-sulfonyl migration is unprecedented and mechanistically intriguing. The synthetically versatile generation of densely functionalised pyrazoles containing substituents amenable to further modification offers advantages over alternative synthetic routes. Isolation of the N-alkylated pyrazoles 11a and 12a as by-products from the cycloaddition through further reaction of the pyrazoles 10 with excess α-diazoacetate, proved useful in rationalising the tautomeric behaviour evident in the NMR spectra of the pyrazoles, with the position of tautomeric equilibrium influenced by solvent and substituents.
Experimental and Modeling Studies on the Solubility of 2-Chloro-N-(4-methylphenyl)propanamide (S1) in Binary Ethyl Acetate + Hexane, Toluene + Hexane, Acetone + Hexane, and Butanone + Hexane Solvent Mixtures Using Polythermal Method
Pascual, Gladys Kate,Donnellan, Philip,Glennon, Brian,Kamaraju, Vamsi Krishna,Jones, Roderick C.
, p. 3193 - 3205 (2017/10/19)
The solubility of 2-chloro-N-(4-methylphenyl)propanamide (S1) in ethyl acetate + hexane mixtures between the temperatures of 273.43 to 327.67 K, in toluene + hexane mixtures from 273.24 to 331.62 K, in acetone + hexane mixtures from 269.81 to 318.8 butano
