Tazofelone → 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-2-thioxo-4-thiazolidinone

Participants

Reaction Steps

The aryl-substituted rhodanine derivatives of formula I are either known in the art or may be prepared by any of a number of well-known procedures. For example, Teuber et al., Leibigs Ann. Chem., 757 (1978) disclose 5-[[3,5-bis(1,1-dimethylethyl)-4hydroxyphenyl]methylene]-2-thioxo-4-thiazolidinone (referred to in the following discussion as Compound A). The compound is prepared by reacting 3,5-di-tert-butyl-4-hydroxybenzaldehyde with rhodanine at reflux temperature in glacial acetic acid using fused sodium acetate as catalyst. 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]-methylene-4-thiazolidinone (Compound B), 5-[[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-4-thiazolidinone (Compound C) and 5-[[3,5-bis (1,1-dimethylethyl)-4-thiazolidinone (Compound D) can be prepared from Compound A as follows.

Provenance & Evidence