Dimethylformamide → 4,4'-Bis(3-formylcarbazol-9-yl)biphenyl

HRID 333571노트

반응식

HRID 333571 반응식
O(Cl)Cl.CN(C)[CH:6]=[O:7].[CH:9]1[C:21]2[N:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][C:31]([N:34]5[C:46]6[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=6[C:40]6[C:35]5=[CH:36][CH:37]=[CH:38][CH:39]=6)=[CH:30][CH:29]=4)=[CH:24][CH:23]=3)[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1.[CH2:47]([OH:49])C.ClCCl>O>[CH:47]([C:11]1[CH:10]=[CH:9][C:21]2[N:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:29]=[CH:30][C:31]([N:34]5[C:46]6[CH:45]=[CH:44][C:43]([CH:6]=[O:7])=[CH:42][C:41]=6[C:40]6[C:35]5=[CH:36][CH:37]=[CH:38][CH:39]=6)=[CH:32][CH:33]=4)=[CH:24][CH:23]=3)[C:19]3[C:14]([C:13]=2[CH:12]=1)=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:49]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24646Chlorine monoxideHCID 112487164,4'-Bis(9H-carbazol-9-yl)biphenylHCID 21584144Dichloromethane ethanol

생성물 1

HCID 426406674,4'-Bis(3-formylcarbazol-9-yl)biphenyl수율 87%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Phosphosphorus oxychloride (13 ml, 21.5 g, 140 mmol) was added dropwise to a stirring mixture of N,N-dimethylformamide (5.40 ml, 5.10 g, 69.7 mmol) and 4,4′-bis(carbazol-9-yl)biphenyl (7.72 g, 16.0 mmol) and the resulting mixture was stirred at room temperature for 5 minutes then heated to 90° C. for 24 h. (nb reaction mixture was followed by TLC using 5% ethanol/dichloromethane as the eluent). The reaction mixture was poured into water (800 ml) and this beaker was placed in the ultrasonic bath for 2 hours to break up the material. The mixture was stirred for a further 2 hours then filtered. The residue was washed with water and then hexane and dried at the pump for 2 hours. The crude product, a brown solid, was heated with acetone (3×400 ml) and filtered. The product was insoluble in most organic solvent. The impurities were removed by washing with acetone. The product, 4,4′-bis(3-formylcarbazol-9-yl)biphenyl, (7.92 g, 87%) was obtained with melting point 295° C. (dec.). Found: C, 81.74; H, 4.71; and N, 4.45. C38H28N2O2. (CH3)2CO requires C, 82.25; H, 5.05; N, 4.68%). 1H n.m.r. (300 MHz, MeeSO): δ 10.09 (2H, s, CHO); 8.88 (2H, d, J 0.88 Hz, aromatic H); 8.41 (2H, d, J 7.61 Hz, aromatic H); 8.41 (4H, d, J 8.40 Hz, aromatic H); 8.00 (2H, dd, J 8.49, 1.46 Hz, aromatic H); 7.83 (4H, d, J 8.49 Hz, aromatic H); 7.38-7.61 (8H, m, aromatic H). λmax(CH2Cl2): 215 nm (ε/Lmol−1 cm−1 9163), 241 (68 488), 272 (65 928), 294 (67 194) 328 (42 620). FT-IR (solid): 3045, 2825, 2730, 1682, 1623, 1591, 1505, 1456, 1438, 1365, 1319, 1275, 1230, 1180, 802, 745 cm−1.

후처리

  1. temperaturethen heated to 90° C. for 24 h. (
  2. customnb reaction mixture
  3. waitthis beaker was placed in the ultrasonic bath for 2 hours
  4. stirringThe mixture was stirred for a further 2 hours
  5. filtrationthen filtered
  6. washThe residue was washed with water
  7. dry with materialhexane and dried at the pump for 2 hours
  8. temperatureThe crude product, a brown solid, was heated with acetone (3×400 ml)
  9. filtrationfiltered
  10. customThe impurities were removed
  11. washby washing with acetone

출처 및 근거

ORD 기록
ord-9bd45bbad56b401bb0b2d9004318e70e
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883321B2

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