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

HRID 467193
ノート
印刷プレビュー

反応式

HRID 467193 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-497c6b6719d64023b6335f10558a652f
出典データセット
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05158966

反応ノート

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