Ammonia → 2,4-dimethyl-1,6-ditetradecylpyridinium Hexafluorophosphate

HRID 272664

Reaktionsgleichung

Reaktionsgleichung von HRID 272664
[F:1][P-:2]([F:7])([F:6])([F:5])([F:4])[F:3].[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[O+]=1.[CH2:30]([NH2:44])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].C(N(CC)CC)C.N>C(Cl)(Cl)Cl.C(O)(=O)C>[F:1][P-:2]([F:7])([F:6])([F:5])([F:4])[F:3].[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[N+:44]=1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 16217TetradecylamineHCID 115396712,4-Dimethyl-6-tetradecylpyrylium hexafluorophosphate

Produkt 1

HCID 115202222,4-dimethyl-1,6-ditetradecylpyridinium HexafluorophosphateAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

2,4-Dimethyl-6-tetradecylpyrylium hexafluorophosphate (10, n=13, 1.5 g, 3.33 mmol) was dissolved in 15 mL chloroform and treated with 0.71 g (3.33 mmol) of tetradecylamine (11, m=13). Triethylamine (0.5 mL) was then added to the brown-yellow solution, which was subsequently refluxed for 5 minutes, treated with 1 mL of acetic acid and refluxed for another hour. The homogenous mixture was treated with 0.2 mL of concentrated aqueous ammonia, refluxed for 5 min., cooled and extracted with 10 mL of water to solve the precipitated inorganic salts. After separation, the chloroform layer was dried on sodium sulfate and evaporated to dryness to yield 2.00 g of crude product. This product was purified by means of flash chromatography (Silica gel 60) using a 20/80 methanol/chloroform (v/v) mobile phase to yield 0.56 g (22%) of pure product, which was recrystallized from ethanol to yield 0.54 g of crystalline compound (12, m=n=13).

Aufarbeitung

  1. temperaturewas subsequently refluxed for 5 minutes
  2. temperaturerefluxed for another hour
  3. temperaturerefluxed for 5 min.
  4. temperaturecooled
  5. extractionextracted with 10 mL of water
  6. customAfter separation
  7. dry with materialthe chloroform layer was dried on sodium sulfate
  8. customevaporated to dryness
  9. customto yield 2.00 g of crude product
  10. customThis product was purified by means of flash chromatography (Silica gel 60)

Quellen und Nachweise

ORD-Eintrag
ord-522d95feea284699ba5b2bcab6c85853
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456197B2

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