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

HRID 467187

Reaktionsgleichung

Reaktionsgleichung von HRID 467187
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][C:20](=[S:22])[NH:19][C:18]2=[O:23])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].C(C1C=C(C=C(C(C)(C)C)C=1O)C=O)(C)(C)C.S1CC(=O)NC1=S.CC(C1C=C(N2C(=O)CSC2=C)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(N1C(=O)C(C(C)(C)C)SC1)(C)C>C(O)(=O)C>[CH3:15][C:12]([C:9]1[CH:8]=[C:7]([CH2:16][CH:17]2[S:21][C:20](=[S:22])[NH:19][C:18]2=[O:23])[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])[CH3:14]

Komponenten

8

Edukt 6

HCID 68745Tazofelone2×HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 1201546RhodanineHCID 30715115-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-thiazolidinoneHCID 572839973,5-Bis (1,1-dimethylethyl)-4-thiazolidinone2×HCID 86746307HCID 86746307, Verbindung2×

Produkt 1

HCID 99683565-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-2-thioxo-4-thiazolidinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3db86b1154fe427fb5a62c4ece6d84ac
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05158966

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