(Aminomethyl)phosphonic acid → 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide

HRID 251512

Reaktionsgleichung

Reaktionsgleichung von HRID 251512
[CH2:1]([N:4]1[C:13](=[O:14])[CH:8]2[CH2:9][CH:10]=[CH:11][CH2:12][CH:7]2[C:5]1=[O:6])[CH:2]=[CH2:3].NCP(=O)(O)[OH:18].O.OO>S([O-])(O)(=O)=O.C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[O:18]1[CH:11]2[CH:10]1[CH2:9][CH:8]1[C:13](=[O:14])[N:4]([CH2:1][CH:2]=[CH2:3])[C:5](=[O:6])[CH:7]1[CH2:12]2

Komponenten

6

Edukt 3

HCID 14017(Aminomethyl)phosphonic acidHCID 449047Hydrogen peroxide waterHCID 13184973N-allyl-4-cyclohexene-1,2-dicarboximide

Produkt 1

HCID 252422084,5-epoxy-N-allylcyclohexane-1,2-dicarboximideAusbeute 1.000,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 150191Sodium Tungstate DihydrateKatalysatorHCID 10939560Methyltricaprylylammonium bisulfateKatalysator

Versuchsvorschrift

In a 50 mL three-necked flask equipped with stirrer, dropping funnel and Dimroth condenser tube there were charged 5.15 g of N-allyl-4-cyclohexene-1,2-dicarboximide, 0.23 g of methyltrioctylammonium hydrogensulfate, 0.22 g of sodium tungstate dihydrate and 0.03 g of aminomethylphosphonic acid. The mixture was heated using an oil bath kept at 90° C., and after adding 4 ml of 30% hydrogen peroxide water dropwise over a period of 30 minutes through a dropping funnel, the mixture was aged for 4 hours. It was then cooled in an ice bath, and after removing the excess hydrogen peroxide with 15 mL of saturated aqueous sodium thiosulfate, extraction was performed 5 times with 10 mL of ethyl acetate. The obtained ethyl acetate solution was dried overnight over anhydrous sodium sulfate, a rotary evaporator was used to remove the ethyl acetate solvent to obtain 3.21 g of a crude product of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide, and then purification was performed by chromatography with a column packed with 25% hydrated silica gel. Structural isomers of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide exist due to the epoxy group, and of these there were obtained 0.72 g of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide 1 and 0.56 g of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide 2. An AL-400 nuclear magnetic resonance apparatus by JEOL Corp. was used to measure the 1H-NMR and 13C-NMR spectra of the 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide 1 in a heavy chloroform solvent, thus allowing confirmation of the structure. The 1H-NMR and 13C-NMR spectra of the 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide 1 are shown in FIGS. 1 and 2, respectively, and the 1H-NMR integral values of the 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide 1 are shown in Table 1 below.

Aufarbeitung

  1. customIn a 50 mL three-necked flask equipped with stirrer
  2. temperatureThe mixture was heated
  3. customkept at 90° C.
  4. temperatureIt was then cooled in an ice bath
  5. customafter removing the excess hydrogen peroxide
  6. extractionwith 15 mL of saturated aqueous sodium thiosulfate, extraction
  7. dry with materialThe obtained ethyl acetate solution was dried overnight over anhydrous sodium sulfate
  8. customa rotary evaporator
  9. customto remove the ethyl acetate solvent
  10. customto obtain 3.21 g of a crude product of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide
  11. custompurification

Quellen und Nachweise

ORD-Eintrag
ord-326ae3cc2a4e4786a8b162abd8b8c073
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863461B2

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