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

HRID 272664

反応式

HRID 272664 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 115202222,4-dimethyl-1,6-ditetradecylpyridinium Hexafluorophosphate収率 26%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-522d95feea284699ba5b2bcab6c85853
出典データセット
uspto-grants-2008_11
特許番号
US07456197B2

関連ノート

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