Six‐Step Continuous Flow Synthesis of Diclofenac Sodium via Cascade Etherification/Smiles Rearrangement Strategy: Tackling the Issues of Batch Processing
hydroxyacetyldiphenylamine operated with the precise control of reaction conditions in continuous flow was realized as the key step in this multistep synthetic chemistry. The undesired amide hydrolysis in Smiles rearrangement was addressed and the extra installation of N-chloroacetyl group in current industrial batch mode was avoided. Diclofenac sodium was obtained in 63 % isolated yield with an average yield
[EN] A PROCESS FOR THE PREPARATION OF N-(2,6-DICHLOROPHENYL)-N-PHENYL-N-(CHLOROACETYL)-AMINE
申请人:LABORATORIO CHIMICO INTERNAZIONALE S.P.A.
公开号:WO1992022522A1
公开(公告)日:1992-12-23
(EN) N-(2,6-dichlorophenyl)-N-phenyl-N-(chloroacetyl)-amine of formula (I) (intermediate for the synthesis of Diclofenac) is prepared by means of rearrangement of N-(2,6-dichlorophenoxyacetyl)-aniline to give N-(2,6-dichlorophenyl)-aniline which, in its turn, is transformed into the final product by reaction with chloroacetyl chloride.(FR) N-(2,6-dichlorophényl)-N-phényl-N-(chloroacétyl)-amine de la formule (I) (intermédiaire utilisé dans la syntèse de Diclofénac) préparée par réarrangement de N-(2,6-dichlorophénoxyacétyl)-aniline pour donner N-(2,6-dichlorophényl)-aniline qui, à son tour, est transformée en produit final par réaction avec du chlorure de chloroacétyle.