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

HRID 273886

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.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]

参加物

実験手順

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.

後処理

temperatureat reflux temperature for one hour
customThe product was isolated
customto the cooled reaction mixture
customseparating the layers
washwashing the organic layer with 1N hydrochloric acid
dry with materiala saturated sodium chloride solution, drying over magnesium sulfate
concentrationconcentrating in vacuo
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-2ac8d950556a4b60a304671f3596435e
出典データセット: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05387690

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 1

実験手順

後処理

出典と根拠

関連ノート