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Hydrochloric Acid → 2-(4-Chloro-3-methoxy-phenoxymethyl)-1-(3,5-dichloro-benzyl)-1H-imidazole

HRID 2101487
Notes
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Reaction equation

HRID 2101487 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.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=1[O:26][CH3:27].C([O-])([O-])=O.[K+].[K+].Cl>O.CS(C)=O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:3][C:4]2[N:5]([CH2:9][C:10]3[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[CH:11]=3)[CH:6]=[CH:7][N:8]=2)=[CH:21][C:20]=1[O:26][CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 110998604-Chloro-3-methoxyphenolHCID 68862721chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride

Product 1

HCID 119517782-(4-Chloro-3-methoxy-phenoxymethyl)-1-(3,5-dichloro-benzyl)-1H-imidazoleYield 97.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a mixture of 2-chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride (see Example 1) (150 mg, 0.5 mmol), 4-chloro-3-methoxyphenol (158 mg, 1 mmol) and DMSO (1 mL) was added K2CO3 (415 mg, 3 mmol). The reaction was stirred at ambient temperature for 8 h before diluting with water (10 mL). A solution of 1N HCl was added until the mixture was 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, hexanes/EtOAc) to afford the title compound (194 mg, 97%) as a white solid: ESI MS m/z 397 [C18H15Cl3N2O2+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, hexanes/EtOAc)

Sources & evidence

ORD record
ord-90060fad463942c5b7cd8a8acbec1de9
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07572921B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes