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

HRID 273886

반응식

HRID 273886 반응식
[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.CC(N=NC(C#N)(C)C)(C#N)C.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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

The title compound was prepared in 71% yield from 10.31 g of the thione of Example 5 upon heating with 38.15 ml of tri-n-butyltin hydride and 1.16 g of azobisisobutyronltrile (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.

후처리

  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

출처 및 근거

ORD 기록
ord-2ac8d950556a4b60a304671f3596435e
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387690

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