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

HRID 583540
Notes
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Reaction equation

HRID 583540 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23978
Copper
Catalyst
HCID 6212ChloroformSolvent

Conditions

Temperature
200 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-92c8721821554ee5abeb0f6e915bc73b
Source dataset
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05929235

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes