Hydrochloric Acid → 3-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenol

HRID 2101483Notes

Reaction equation

HRID 2101483 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]([CH2:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[CH:11]=2)[CH:6]=[CH:7][N:8]=1.[C:18]1([CH:25]=[CH:24][CH:23]=[C:21]([OH:22])[CH:20]=1)[OH:19].C([O-])([O-])=O.[K+].[K+].Cl>O.CS(C)=O>[Cl:17][C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([Cl:16])[CH:13]=1)[CH2:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[CH2:3][O:19][C:18]1[CH:20]=[C:21]([OH:22])[CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 11430Potassium CarbonateHCID 68862721chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride

Product 1

HCID 119510733-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenolYield 65%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a mixture of 2-chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride (156 mg, 0.5 mmol), resorcinol (330 mg, 3.0 mmol) and DMSO (1 mL) was added K2CO3 (691 mg, 5.0 mmol). The reaction was stirred at ambient temperature for 14 h before diluting with water (20 mL). A solution of 1N HCl was added until the mixture was made only slightly basic (pH 8) before extracting with EtOAc (30 mL). The EtOAc phase was washed with water (10 mL), dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 1:2 to 1:3 hexane/EtOAc then 100% EtOAc) to provide the title compound (113 mg, 65%) as an off-white solid: ESI MS m/z 349 [C17H14Cl2N2O2+H]+.

Workup

  1. extractionbefore extracting with EtOAc (30 mL)
  2. washThe EtOAc phase was washed with water (10 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, 1:2 to 1:3 hexane/EtOAc

Sources & evidence

ORD record
ord-1b6ea19ea0f344b0bbee4ba4add27a7a
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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