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

HRID 2101502Notes

Reaction equation

HRID 2101502 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[ClH:7].Cl[CH2:9][C:10]1[N:11]([CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)[CH:12]=[CH:13][N:14]=1.CN([CH:27]=[O:28])C>>[Cl:7][C:17]1[CH:18]=[C:27]([CH:20]=[C:21]([O:4][CH3:1])[CH:16]=1)[O:28][CH2:9][C:10]1[N:11]([CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)[CH:12]=[CH:13][N:14]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 68862721chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride

Product 1

HCID 119514242-(3-Chloro-5-methoxy-phenoxymethyl)-1-(3,5-dichloro-benzyl)-1H-imidazoleYield 49%

Procedure

3,-Chloro-5-methoxy-1-phenol was dissolved in anhydrous DMF and K2CO3 was added. The reaction mixture was stirred at room temperature for 15 min and chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride (see Example 1) was added to the reaction mixture. The resulting mixture was stirred at room temperature for 36 h. The mixture was diluted with FtOAc and washed with water (×2). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was then purified by silica gel prep TLC using CH2Cl2:MeOH 98:2 as an eluent to afford the title compound (56 mg, 49%); MS m/z 397 [C18H15Cl3N2O2+H]+.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 36 h
  2. additionThe mixture was diluted with FtOAc
  3. washwashed with water (×2)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting residue was then purified by silica gel prep TLC

Sources & evidence

ORD record
ord-d295cfdd13294eb5b7658c31d80aa5bb
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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