Tazofelone → 5-[[3,5-Bis(1-methylethyl)-4-hydroxyphenyl]methylene]-3-methyl-4-thiazolidinone

HRID 2935

Reaction equation

HRID 2935 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][C:20](=S)[NH:19][C:18]2=[O:23])[CH:8]=[C:9]([C:12](C)([CH3:14])[CH3:13])[C:10]=1[OH:11])(C)[CH3:3].[C:24](C1C=C(C=C(C(C)(C)C)C=1O)C=O)(C)(C)C.S1CC(=O)NC1=S.CC(C1C=C(C=C2SCNC2=O)C=C(C(C)(C)C)C=1O)(C)C.CC(C1C=C(CC2SCNC2=O)C=C(C(C)(C)C)C=1O)(C)C.CC(C1C=C(CC2SC(=S)NC2=O)C=C(C(C)(C)C)C=1O)(C)C>C(O)(=O)C>[CH3:3][CH:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][CH2:20][N:19]([CH3:24])[C:18]2=[O:23])[CH:8]=[C:9]([CH:12]([CH3:13])[CH3:14])[C:10]=1[OH:11])[CH3:1]

Participants

8

Reactant 6

HCID 68745Tazofelone2×HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 1300035-(3,5-Bis(tert-butyl)-4-hydroxyphenyl)methylene-4-thiazolidinone2×HCID 1201546RhodanineHCID 30715115-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-thiazolidinoneHCID 99683565-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-2-thioxo-4-thiazolidinone2×

Product 1

HCID 540784545-[[3,5-Bis(1-methylethyl)-4-hydroxyphenyl]methylene]-3-methyl-4-thiazolidinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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)-4-hydroxyphenyl]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-hydroxyphenyl]methyl]-2-thioxo -4-thiazolidinone (Compound D) can be prepared from Compound A as follows.

Workup

  1. custommay be prepared by any of a number of well-known procedures
  2. customThe compound is prepared

Sources & evidence

ORD record
ord-f5393e1cc6454a74b09650aa083904a0
Source dataset
uspto-grants-1998_03
Patent number
US05731336

Linked notes

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