Potassium Iodide → Methyl 4'-[2-({8-[2-(acetylamino)ethyl]-2-naphthyl}oxy)ethoxy]-[1,1'-biphenyl]-4-carboxylate

HRID 1373480Notes

Reaction equation

HRID 1373480 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:19][CH2:20][O:21][C:22]1[CH:31]=[C:30]2[C:25]([CH:26]=[CH:27][CH:28]=[C:29]2[CH2:32][CH2:33][NH:34][C:35](=[O:37])[CH3:36])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CS(C)=O.CC(=O)CC.O>[C:35]([NH:34][CH2:33][CH2:32][C:29]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:30]=1[CH:31]=[C:22]([O:21][CH2:20][CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=3)=[CH:6][CH:7]=1)[CH:23]=[CH:24]2)(=[O:37])[CH3:36]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1490289Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylateHCID 11175075HCID 11175075, compound

Product 1

HCID 15540840Methyl 4'-[2-({8-[2-(acetylamino)ethyl]-2-naphthyl}oxy)ethoxy]-[1,1'-biphenyl]-4-carboxylate

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a 100 ml round-bottomed flask, 0.003 mol of methyl 4′-hydroxy[1,1′-biphenyl]-4-carboxylate and 0.003 mol of the compound obtained in Step A are dissolved in a mixture of 3 ml of dimethyl sulphoxide and 20 ml of butanone. 0.009 mol of potassium carbonate and one potassium iodide crystal are added and then the mixture is heated at reflux for 12 hours. The reaction mixture is then cooled and poured into 100 ml of water. The precipitate that forms is suctioned off and recrystallised to yield the title product.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 12 hours
  3. temperatureThe reaction mixture is then cooled
  4. customrecrystallised

Sources & evidence

ORD record
ord-e9f724904f044cb9b566348c26eab9c9
Source dataset
uspto-grants-2007_01
Patent number
US07161035B2

Reaction notes

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