Sulfuric Acid → 1,7-Diacetamido-3,5-dimethyladamantane

HRID 2084732

Reaktionsgleichung

Reaktionsgleichung von HRID 2084732
[C:1]([NH:4][C:5]12[CH2:14][C:9]3([CH3:15])[CH2:10][CH:11]([CH2:13][C:7]([CH3:16])([CH2:8]3)[CH2:6]1)[CH2:12]2)(=[O:3])[CH3:2].S(=O)(=O)(O)O.[OH-:22].[Na+].[C:24](#[N:26])[CH3:25]>>[C:1]([NH:4][C:5]12[CH2:14][C:9]3([CH3:15])[CH2:10][C:11]([NH:26][C:24](=[O:22])[CH3:25])([CH2:13][C:7]([CH3:16])([CH2:8]3)[CH2:6]1)[CH2:12]2)(=[O:3])[CH3:2]

Komponenten

5

Edukt 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 5276209N-(3,5-dimethyl-1-adamantyl)acetamide

Produkt 1

HCID 28424991,7-Diacetamido-3,5-dimethyladamantane

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-Acetamido-3,5-dimethyladamantane (2) (10 g) was added slowly to concentrated sulfuric acid (120 mL) cooled to 0° C. in a salt-ice bath. The solution was stirred at 0° C. for 1 h. Acetonitrile (23 mL) was then added dropwise. The reaction mixture was stirred at 0° C. for 2 h, and then at room temperature for 1 h. The reaction mixture was poured into ice-water. Saturated sodium hydroxide solution was added with cooling. The precipitate (dark solid) was filtered, and discarded. The off-white solid was collected by filtration. Recrystallization afforded 3 as a white solid (6.3 g).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 0° C. for 2 h
  2. waitat room temperature for 1 h
  3. temperaturewith cooling
  4. filtrationThe precipitate (dark solid) was filtered
  5. filtrationThe off-white solid was collected by filtration
  6. customRecrystallization

Quellen und Nachweise

ORD-Eintrag
ord-4aa777740039406abe6a9dae143ce130
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06717012B2

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