Sulfuric Acid → N-(3-hydroxy-5,7-dimethyl-1-adamantyl)acetamide

HRID 1167867

Reaktionsgleichung

Reaktionsgleichung von HRID 1167867
[OH:1]S(O)(=O)=O.[C:6]([NH:9][C:10]12[CH2:19][C:14]3([CH3:20])[CH2:15][CH:16]([CH2:18][C:12]([CH3:21])([CH2:13]3)[CH2:11]1)[CH2:17]2)(=[O:8])[CH3:7]>>[C:6]([NH:9][C:10]12[CH2:19][C:14]3([CH3:20])[CH2:15][C:16]([OH:1])([CH2:18][C:12]([CH3:21])([CH2:13]3)[CH2:11]1)[CH2:17]2)(=[O:8])[CH3:7]

Komponenten

3

Edukt 2

HCID 1118Sulfuric AcidHCID 5276209N-(3,5-dimethyl-1-adamantyl)acetamide

Produkt 1

HCID 2843103N-(3-hydroxy-5,7-dimethyl-1-adamantyl)acetamide

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Fuming H2SO4 (3 mL) was added to 1-acetamido-3,5-dimethyladamantane (0.2 g) at 0° C. under nitrogen and the reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was poured onto ice (10 g) and the product was extracted with ether (10 mL×4). The combined ether solution was washed with brine (10 mL) and water (10 mL). The solution was dried using sodium sulfate. The solvent was removed in vacuo and, after crystallization on standing, 70 mg of white product was obtained. Pure product was obtained by recrystallization in ether. 1H NMR (DMSO-d6, ppm): 7.30 (brs, 1 H, NH), 4.37 (brs, 1 H, OH), 1.72 (s, 3 H, COCH3), 1.65 (s, 2 H), 1.47 (s, 4 H), 1.24-1.14 (dd, 4 H, J=11.2, 23.9 Hz), 0.99 (s, 2 H), 0.82 (s, 6 H, 2×CH3). m.p. 194-195° C. Anal. (C14H23NO2), C. H. N.

Aufarbeitung

  1. additionThe reaction mixture was poured onto ice (10 g)
  2. extractionthe product was extracted with ether (10 mL×4)
  3. washThe combined ether solution was washed with brine (10 mL) and water (10 mL)
  4. customThe solution was dried
  5. customThe solvent was removed in vacuo
  6. customafter crystallization

Quellen und Nachweise

ORD-Eintrag
ord-f9f3448b52af46029ec7036b7052b2ad
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620845B2

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