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

HRID 1373378

반응식

HRID 1373378 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

실험 절차

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. Extracton 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).

후처리

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

출처 및 근거

ORD 기록
ord-3653ddffd74140168f7cc0c3dd0b06fe
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07161005B2

연결된 노트

불러오는 중…