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

HRID 272664

반응식

HRID 272664 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6212Chloroform용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-522d95feea284699ba5b2bcab6c85853
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456197B2

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