3-Aminophenol → 3-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenylamine

HRID 2101518Notes

Reaction equation

HRID 2101518 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl.Cl[CH2:13][C:14]1[N:15]([CH2:19][C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)[CH:16]=[CH:17][N:18]=1>CN(C=O)C>[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[C:24]([Cl:26])[CH:23]=1)[CH2:19][N:15]1[CH:16]=[CH:17][N:18]=[C:14]1[CH2:13][O:8][C:4]1[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 115683-AminophenolHCID 24758Sodium hydrideHCID 68862721chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride

Product 1

HCID 119510703-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenylamineYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Aminophenol (87 mg, 0.8 mmol) was dissolved in DMF and NaH (33 mg, 0.83 mmol) was added. After 10 min, 2-(chloromethyl)-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride (see Example 1) (100 mg, 0.32 mmol) was added in one portion. After 20 min, the reaction was partitioned between water (10 mL) and EtOAc (10 mL). The layers were separated and the aqueous layer was re-extracted with EtOAc (1×10 mL). The combined organic layers were washed with 1M NaOH (3×10 mL), water (10 mL) and brine, dried over MgSO4, filtered and concentrated to yield the title compound as a pale yellow oil (78 mg, 70%); MS m/z 348 [C17H15Cl2N3O+H]+.

Workup

  1. waitAfter 20 min
  2. customthe reaction was partitioned between water (10 mL) and EtOAc (10 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was re-extracted with EtOAc (1×10 mL)
  5. washThe combined organic layers were washed with 1M NaOH (3×10 mL), water (10 mL) and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-677a91aa325b4fada7c1c34c13ba73ce
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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