Imidazole → HCID 69328000, compound

HRID 1168669Notes

Reaction equation

HRID 1168669 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:14][OH:15])[CH:7]=[CH:8][C:9]=1NCCC)([O-:3])=[O:2].N1[CH:20]=[CH:19][N:18]=C1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].[CH3:29]N(C=O)C>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:14][O:15][Si:21]([CH3:23])([CH3:22])[C:24]([CH3:27])([CH3:26])[CH3:25])[CH:7]=[CH:8][C:9]=1[CH2:29][CH2:20][CH2:19][NH2:18])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 22270272HCID 22270272, compound

Product 1

HCID 69328000HCID 69328000, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 20 g (0.095 mole) of [3-nitro-4-(propylamino)phenyl]methan-1-ol and 19.2 g (0.28 mole) of imidazole in 200 mL of anhydrous DMF is treated with 19 g (0.13 mole) of t-butyldimethylsilyl chloride at room temperature for 30 min. The resulting mixture is diluted with 400 mL of ethyl acetate and washed 3×200 mL of water and 1×200 mL of brine. The resulting orgainc layer is dried over anhydrous Na2SO4 and the solvent removed in vacuo. The resulting oil is column chromatographed 5% ethyl acetate/hexanes to afford 11 g (35%) of {2-nitro-4-[(1,1,2,2-tetramethy-1-silapropoxy)methyl]phenyl}propylamine.

Workup

  1. washwashed 3×200 mL of water and 1×200 mL of brine
  2. dry with materialThe resulting orgainc layer is dried over anhydrous Na2SO4
  3. customthe solvent removed in vacuo
  4. customchromatographed 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-cf7e51a9c3e2475fad5afd251e6dbf68
Source dataset
uspto-grants-2003_09
Patent number
US06627624B1

Reaction notes

Loading…