Potassium Carbonate → HCID 19708511, compound

HRID 725746Notes

Reaction equation

HRID 725746 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][C:15]1[CH:16]=[C:17]([C:22]2[CH:27]=[CH:26][C:25](I)=[C:24]([CH3:29])[CH:23]=2)[CH:18]=[CH:19][C:20]=1[I:21].C(=O)([O-])[O-].[K+].[K+]>[Cu].[N+](C1C=CC=CC=1)([O-])=O>[CH3:29][C:24]1[CH:23]=[C:22]([C:17]2[CH:18]=[CH:19][C:20]([I:21])=[C:15]([CH3:14])[CH:16]=2)[CH:27]=[CH:26][C:25]=1[N:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11487DiphenylamineHCID 223236094,4'-Diiodo-3,3'-dimethyl-1,1'-biphenyl

Product 1

HCID 19708511HCID 19708511, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7416NitrobenzeneSolvent

Procedure

20.3 g (0.12 mol) of diphenylamine, 65.1 g (0.15 mol) of 3,3'-dimethyl-4,4'-diiodobiphenyl, 19.3 g (0.14 mol) of anhydrous potassium carbonate, 1.52 g (0.024 mol) of copper powder, and 20 ml of nitrobenzene were mixed. The reaction mixture was then allowed to undergo reaction at a temperature of 190° C. to 205° C. for 21 hours. The reaction product was then extracted with 200 ml of toluene. The insoluble contents were removed by filtration. The filtrate was then concentrated to dryness. The concentrate was then purified by column chromatography (carrier: silica gel; elute: 2/7 mixture of toluene and n-hexane) to obtain 32.6 g (yield: 57.2%) of N-(3,3'-dimethyl-4'-iodo-4-biphenylyl)-N,N-diphenylamine.

Workup

  1. customreaction at a temperature of 190° C. to 205° C. for 21 hours
  2. extractionThe reaction product was then extracted with 200 ml of toluene
  3. customThe insoluble contents were removed by filtration
  4. concentrationThe filtrate was then concentrated to dryness
  5. customThe concentrate was then purified by column chromatography (carrier: silica gel; elute: 2/7 mixture of toluene and n-hexane)

Sources & evidence

ORD record
ord-c7517e6b1b434c73acc77f86d5acd191
Source dataset
uspto-grants-1998_01
Patent number
US05707747

Reaction notes

Loading…