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

HRID 583540

反応式

HRID 583540 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 6212Chloroform溶媒

反応条件

温度
200 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-92c8721821554ee5abeb0f6e915bc73b
出典データセット
uspto-grants-1999_07
特許番号
US05929235

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