Phosphorus pentachloride → 4'-Chloro-2,2':6',2''-terpyridine

HRID 640664

反応式

HRID 640664 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:10][C:11](=O)[CH:12]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:21]>P(Cl)(Cl)(Cl)=O>[Cl:21][C:11]1[CH:12]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:10]=1

参加物

4

反応物 2

HCID 24819Phosphorus pentachlorideHCID 6193532,6-Bis(2-pyridyl)-4(1H)-pyridone

生成物 1

HCID 6677484'-Chloro-2,2':6',2''-terpyridine

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

A mixture of 3.99 g (16 mmol) of 1′H-[2,2′;6′,2″]terpyridin-4′-one (L1) and 8.0 g (38 mmol) of phosphorus pentachloride is boiled at reflux in 200 ml of phosphorus oxychloride for sixteen hours. The mixture is allowed to cool and concentrated to dryness. 200 ml of ice-water are then added cautiously to the residue, and the solution is then adjusted to pH 9 with aqueous potassium hydroxide solution. Extraction is carried out three times using chloroform and the organic extracts are dried over sodium sulfate, filtered and concentrated. After recrystallisation from ethanol, 4′-chloro-[2,2′;6′,2″]terpyridine is obtained in the form of white needles. 1H-NMR (CDCl3, 360 MHz): 7.20-7.29 (m, 2H); 7.70-7.79 (tm, 2H); 8.37 (s, 2H); 8.47 (d, 2H, 7.6 Hz); 8.56-8.63 (dm, 2H).

後処理

  1. temperatureto cool
  2. concentrationconcentrated to dryness
  3. addition200 ml of ice-water are then added cautiously to the residue
  4. extractionExtraction
  5. dry with materialthe organic extracts are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customAfter recrystallisation from ethanol

出典と根拠

ORDレコード
ord-fb9ba4591b4a4305b522dcec802bb6fb
出典データセット
uspto-grants-2010_04
特許番号
US07692004B2

関連ノート

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