Water → 5-(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)methylene-N-methyl-4-thiazolidinone

HRID 467193

Reaktionsgleichung

Reaktionsgleichung von HRID 467193
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][C:20](=S)[N:19]([CH3:23])[C:18]2=[O:24])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N.O>C1(C)C=CC=CC=1>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][CH2:20][N:19]([CH3:23])[C:18]2=[O:24])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:1])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 543896015-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-methyl-2-thioxo-4-thiazolidinone

Produkt 1

HCID 1300015-(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)methylene-N-methyl-4-thiazolidinoneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

The title compound was prepared in 71% yield from 10.31 g of the thione of Example 9 upon heating with 38.15 ml of tri-n-butyl tin hydride and 1.16 g of azobisisobutyronitrile (AIBN) in 142 ml of toluene at reflux temperature for one hour. The product was isolated by adding water to the cooled reaction mixture, separating the layers, washing the organic layer with 1N hydrochloric acid and a saturated sodium chloride solution, drying over magnesium sulfate, concentrating in vacuo, and purifying the residue by chromatography over silica gel eluting with a 10-50% hexane in ethyl acetate gradient. The purified product had a melting point of 142-144° C.

Aufarbeitung

  1. temperatureat reflux temperature for one hour
  2. customThe product was isolated
  3. customto the cooled reaction mixture
  4. customseparating the layers
  5. washwashing the organic layer with 1N hydrochloric acid
  6. dry with materiala saturated sodium chloride solution, drying over magnesium sulfate
  7. concentrationconcentrating in vacuo
  8. custompurifying the residue by chromatography over silica gel eluting with a 10-50% hexane in ethyl acetate gradient

Quellen und Nachweise

ORD-Eintrag
ord-497c6b6719d64023b6335f10558a652f
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05158966

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