Hydrochloric Acid → HCID 178494765, compound

HRID 1946962Notes

Reaction equation

HRID 1946962 reaction equation
CN(C)S([N:6]1[CH:10]=[C:9]([CH:11]([O:19][CH3:20])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]=[C:7]1[Si](C(C)(C)C)(C)C)(=O)=O.Cl.[OH-].[Na+]>C(O)C.O>[CH3:20][O:19][CH:11]([C:9]1[N:8]=[CH:7][NH:6][CH:10]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59742753HCID 59742753, compound

Product 1

HCID 178494765HCID 178494765, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 2-(tert-butyl-dimethyl-silanyl)-4-(1-methoxy-2-phenyl-ethyl)-imidazole-1-sulfonic acid dimethylamide (105 mg) at r.t. in ethanol (3 ml) under an argon atmosphere was added 2 N HCl (3 ml). The mixture was heated to reflux for 3 hours. The mixture was cooled to r.t. and concentrated to leave a light yellow solid which was taken up in H2O and brought to pH 12 by the addition of 4 N NaOH. The product was extracted with CH2Cl2/MeOH 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/MeOH 9:1) to give 4-(1-methoxy-2-phenyl-ethyl)-1H-imidazole (38 mg) as white solid. MS (ISP): 203.4 ([M+H]+)

Workup

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

Sources & evidence

ORD record
ord-fe1ea2e6aa5f41a1b8b4fe1288adffa9
Source dataset
uspto-grants-2013_03
Patent number
US08399463B2

Reaction notes

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