Sulfuric Acid → 4-[(cyclohexylamino)methyl]-3,3-diphenyldihydro-2(3H)-furanone

HRID 614271

Reaktionsgleichung

Reaktionsgleichung von HRID 614271
[CH:1]1([N:7]2[CH2:10][CH:9]([C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:12]#N)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)[OH:27].[OH-:31].[Na+]>>[CH:1]1([NH:7][CH2:8][CH:9]2[CH2:10][O:31][C:12](=[O:27])[C:11]2([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 12822284alpha-(1-Cyclohexyl-3-azetidinyl)-alpha,alpha-diphenylacetonitrile

Produkt 1

HCID 128222864-[(cyclohexylamino)methyl]-3,3-diphenyldihydro-2(3H)-furanoneAusbeute 20 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To 41.0 g. (0.12 mole) of α-(1-cyclohexyl-3-azetidinyl)-α,α-diphenylacetonitrile was added 100 g. of a 70% solution of sulfuric acid, and the mixture was stirred and heated at 120° C. for 48 hrs. The solution was then poured over ice and made basic with 50% sodium hydroxide, and extracted with chloroform. The organic layer was dried, filtered, and concentrated in vacuo. The residue was crystallized twice from isopropyl ether, the crystallized material weighed 8.0 g. (20% yield) and melted at 129°-131° C.

Aufarbeitung

  1. additionThe solution was then poured over ice
  2. extractionextracted with chloroform
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized twice from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1eea2ad946374144a1393b060f150e92
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04144245

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