Hydrochloric Acid → 2-[2-(3-chloro-phenyl)-2-methoxy-ethyl]-1H-imidazole

HRID 2266777Notes

Reaction equation

HRID 2266777 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([O:34][CH3:35])[CH2:9][C:10]2[N:11](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([O:34][CH3:35])[CH2:9][C:10]2[NH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59599696HCID 59599696, compound

Product 1

HCID 249559872-[2-(3-chloro-phenyl)-2-methoxy-ethyl]-1H-imidazoleYield 0.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 2-[2-(3-chloro-phenyl)-2-methoxy-ethyl]-1-trityl-1H-imidazole (0.24 g) at room temperature in ethanol (2 ml) under an argon atmosphere was added 2 N HCl (3 ml). The mixture was heated to reflux. Stirring was continued for 3 hours. The mixture was cooled to room temperature and concentrated to leave a light yellow solid. This was taken up in H2O and brought to pH=12 by the addition of 4 N NaOH. The product was extracted with CH2Cl2/methanol 4:1. The combined organics were dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient:CH2Cl2→CH2Cl2/methanol 9:1) to give 2-[2-(3-chloro-phenyl)-2-methoxy-ethyl]-1H-imidazole (0.11 mg) as light yellow gum. MS 237.1 ([M+H]+)

Workup

  1. temperatureThe mixture was heated to reflux
  2. concentrationconcentrated
  3. customto leave a light yellow solid
  4. extractionThe product was extracted with CH2Cl2/methanol 4:1
  5. dry with materialThe combined organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (silica gel; gradient:CH2Cl2→CH2Cl2/methanol 9:1)

Sources & evidence

ORD record
ord-6daac0607d3642119bc7ac62aa010d54
Source dataset
uspto-grants-2010_12
Patent number
US07858653B2

Reaction notes

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