Potassium Carbonate → HCID 86744826, compound

HRID 1493503Notes

Reaction equation

HRID 1493503 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[NH:12][C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:20].C(=O)([O-])[O-].[K+].[K+].[O:28]([C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH2:38]Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[Cl:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=1[NH:12][C:6]1[CH:7]=[CH:8][C:9]([O:11][CH2:38][C:37]2[CH:40]=[CH:41][CH:42]=[C:35]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:36]=2)=[CH:10][C:5]=1[CH2:4][C:3]([OH:2])=[O:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 932913-Phenoxybenzyl chlorideHCID 15678649HCID 15678649, compound

Product 1

HCID 86744826HCID 86744826, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[(2,6-dichlorophenyl)amino]-5-hydroxy benzene acetic acid methyl ester (2.5 g, 7.67 mmol) of Example 2F, powdered anhydrous potassium carbonate (0.55 g, 4 mmol), tetrabutylammonium iodide (0.050 g) and dry acetonitrile (50 mL) is stirred at room temperature under nitrogen for 30 min. To the slurry is then added 3-phenoxybenzylchloride (2 g, 9.17 mmol) and the mixture is placed in an oil bath maintained at 65°-70° C. overnight. The solvent is removed and the residue partitioned between water and ethyl acetate (50 mL each). The organic phase is washed with brine and dried (Na2SO4). The solvent is evaporated and the residue (brown oil, 4.2 g) is purified by flash chromatography (on silica Merck 60, hexane-ethyl acetate 85:15) to give the title product (yellow oil, 2.83 g, 73%).

Workup

  1. temperaturemaintained at 65°-70° C. overnight
  2. customThe solvent is removed
  3. customthe residue partitioned between water and ethyl acetate (50 mL each)
  4. washThe organic phase is washed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent is evaporated
  7. customthe residue (brown oil, 4.2 g) is purified by flash chromatography (on silica Merck 60, hexane-ethyl acetate 85:15)

Sources & evidence

ORD record
ord-c273184d4c93491895d68d38db3b16af
Source dataset
uspto-grants-1991_06
Patent number
US05021576

Reaction notes

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