Decalin → 5-(4'-Iodobiphenyl-4-yl)dibenz[b,f]azepine

HRID 583540

반응식

HRID 583540 반응식
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[I:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26](I)=[CH:25][CH:24]=2)=[CH:19][CH:18]=1.[OH-].[K+].C1C2C(CCCC2)CCC1>[Cu].C(Cl)(Cl)Cl>[I:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([N:6]3[C:7]4[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=4[CH:9]=[CH:10][C:11]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]3=4)=[CH:25][CH:24]=2)=[CH:21][CH:22]=1

참가 물질

7

반응물 4

HCID 7044DecalinHCID 9212Dibenz(b,f)azepineHCID 14797Potassium HydroxideHCID 763484,4'-Diiodo-1,1'-biphenyl

생성물 1

HCID 213110775-(4'-Iodobiphenyl-4-yl)dibenz[b,f]azepine수율 50%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 6212Chloroform용매

반응 조건

온도
200 °C

실험 절차

5H-Dibenz[b,f]azepine in an amount of 20.0 g (0.10 mol), 4,4'-diiodobiphenyl in an amount of 60.9 g (0.15 mol), potassium hydroxide in an amount of 6.7 g (0.12 mol) and a copper powder in an amount of 1.3 g (0.02 mol) were mixed with 20 ml of decalin, and heated with stirring in a stream of nitrogen for 36 hours at the external temperature of 200° C. After cooling to room temperature or its vicinity, the reaction solution was admixed with chloroform, and subjected to Celite filtration to remove the insoluble matter. The filtrate was concentrated, and the concentrated solution was purified by column chromatography on silica gel. Thus, 23.6 g of 5-(4'-iodobiphenyl-4-yl)dibenz[b,f]azepine was obtained (in a 50% yield).

후처리

  1. temperatureheated
  2. temperatureAfter cooling to room temperature
  3. filtrationsubjected to Celite filtration
  4. customto remove the insoluble matter
  5. concentrationThe filtrate was concentrated
  6. customthe concentrated solution was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-92c8721821554ee5abeb0f6e915bc73b
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929235

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