Imidazole → 5-Tert-butyl-2-methoxy-3-trimethylsilanyloxymethyl-phenylamine

HRID 2360515Notes

Reaction equation

HRID 2360515 reaction equation
[NH2:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.N1C=CN=C1.[CH3:21][Si:22](Cl)([CH3:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[C:8]([C:6]1[CH:5]=[C:4]([CH2:12][O:13][Si:22]([CH3:24])([CH3:23])[CH3:21])[C:3]([O:14][CH3:15])=[C:2]([NH2:1])[CH:7]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 11430Potassium CarbonateHCID 58366895(3-Amino-5-tert-butyl-2-methoxyphenyl)methanol

Product 1

HCID 584939805-Tert-butyl-2-methoxy-3-trimethylsilanyloxymethyl-phenylamine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.03 g (3-amino-5-tert-butyl-2-methoxy-phenyl)-methanol and 2.4 g imidazole are dissolved in 20 ml of tetrahydrofuran and 2.75 ml trimethylsilyl chloride are added dropwise thereto. The mixture is stirred for 2 hours at ambient temperature, the solvents are eliminated in vacuo and the residue is divided between 10% aqueous potassium carbonate solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5 to 50:50).

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. washthe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialAfter drying with magnesium sulphate the solvents
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5 to 50:50)

Sources & evidence

ORD record
ord-50a7c7795a154655ab5135856a7a4dc1
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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