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

HRID 2940

Reaktionsgleichung

Reaktionsgleichung von HRID 2940
[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-867855b5cbc343afbf6e7d8206f20441
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731336

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