4-Phenoxyphenol → HCID 14402693, compound

HRID 2081644Notes

Reaction equation

HRID 2081644 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl[CH2:20][N:21]1[C:25]([Cl:26])=[C:24]([Cl:27])[N:23]=[CH:22]1>CN(C)C=O.O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:20][N:21]2[C:25]([Cl:26])=[C:24]([Cl:27])[N:23]=[CH:22]2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 132544-PhenoxyphenolHCID 24758Sodium hydrideHCID 144026921H-Imidazole, 4,5-dichloro-1-(chloromethyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 14402693HCID 14402693, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

9.3 g of 4-phenoxyphenol is dissolved in 60 ml of anhydrous dimethylformamide. 1.58 g of 80% strength sodium hydride is added, and the mixture is heated at 60° C. until no more hydrogen evolves (about 1 hour). A solution of 9.28 g of N-(1-chloromethyl)-4,5-dichloroimidazole in 30 ml of dimethylformamide is then dripped in. The mixture is stirred overnight at room temperature, after which it is poured into 500 ml of water, followed by extraction three times with methyl tert-butyl ether. The combined organic phases are washed three times with water, dried over sodium sulfate, and freed from solvent under reduced pressure. The solid residue is recrystallized from n-pentane/ether (6:1) to give N-[(p-phenoxyphenoxy)-methyl]-4,5-dichloroimidazole, m.p.: 82°-83° C.

Workup

  1. custom(about 1 hour)
  2. extractionfollowed by extraction three times with methyl tert-butyl ether
  3. washThe combined organic phases are washed three times with water
  4. dry with materialdried over sodium sulfate
  5. customThe solid residue is recrystallized from n-pentane/ether (6:1)

Sources & evidence

ORD record
ord-8795a4618e1841a789077ff664f33c2a
Source dataset
uspto-grants-1993_02
Patent number
US05185359

Reaction notes

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