Boron trifluoride → HCID 14726544、化合物

HRID 1591131

反応式

HRID 1591131 の反応式
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](Cl)=[O:15])[CH:5]=[CH:4][C:3]1=2.[CH3:18][C:19]1[CH:28]=[CH:27][C:22]([C:23](=[N:25]O)[NH2:24])=[CH:21][CH:20]=1.B(F)(F)F>O1CCOCC1>[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[O:15][N:25]=[C:23]([C:22]4[CH:27]=[CH:28][C:19]([CH3:18])=[CH:20][CH:21]=4)[N:24]=3)[CH:5]=[CH:4][C:3]1=2

参加物

5

反応物 3

HCID 6356Boron trifluorideHCID 209113N'-Hydroxy-4-methylbenzenecarboximidamideHCID 27954665,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl chloride

生成物 1

HCID 14726544HCID 14726544、化合物収率 30.8%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

8.0 g (30 millimoles) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl chloride and 4.5 g (30 millimoles) of 4-methylbenzamidoxime in 250 ml of dioxane were refluxed for 1 hour. 1 ml of boron trifluoride dietherate were added and refluxing was continued for a further 4 hours. The mixture was allowed to cool, poured onto ice/water and extracted with methylene chloride. The organic phase was washed several times with water, dried over magnesium sulfate and evaporated down. The oily residue was purified by column chromatography (silica gel; n-heptane +0.5% of ethyl acetate), and the crude product obtained from the first fractions was recrystallized from methanol to give 3.2 g of the title compound of melting point 106°-109° C.

後処理

  1. temperaturerefluxing
  2. temperatureto cool
  3. additionpoured onto ice/water
  4. extractionextracted with methylene chloride
  5. washThe organic phase was washed several times with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated down
  8. customThe oily residue was purified by column chromatography (silica gel; n-heptane +0.5% of ethyl acetate)
  9. customthe crude product obtained from the first fractions
  10. customwas recrystallized from methanol

出典と根拠

ORDレコード
ord-25a3dc77360b43928a370c152e2080b9
出典データセット
uspto-grants-1993_04
特許番号
US05206242

関連ノート

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