Imidazole → 3-((Tert-butyldimethylsilyl)oxy)aniline

HRID 1910296Notes

Reaction equation

HRID 1910296 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.CN(C=O)C.[NH2:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1>O>[Si:1]([O:26][C:22]1[CH:21]=[C:20]([NH2:19])[CH:25]=[CH:24][CH:23]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 115683-AminophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 143147823-((Tert-butyldimethylsilyl)oxy)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250 mL, three-neck, round bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with tert-butyldimethylsilyl chloride (12.5 g, 82.8 mmol), imidazole (7.64 g, 112 mmol), and anhydrous DMF (60 mL). 3-aminophenol (10.0 g, 91.7 mmol) was added to the resulting solution. After stirring for 12 h at ambient temperature, the reaction mixture was poured into water (300 mL). The resulting suspension was extracted with hexanes (3×300 mL), and the extracts were combined, dried over sodium sulfate, and filtered. Concentration of the filtrate followed by column chromatography gave compound 122 as a light yellow oil. 1H NMR (DMSO-d6) δ (ppm), 6.84 (t, 1H, J=7.9 Hz), 6.16 (d, 1H, J=6.7 Hz), 6.10 (m, 1H), 5.97 (d, 1H, J=9.1 Hz), 4.98 (s, 2H), 0.95 (s, 9H), 0.16 (s, 6H); m/z=224 (M+H).

Workup

  1. customA 250 mL, three-neck, round bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. extractionThe resulting suspension was extracted with hexanes (3×300 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-82b01cfe601f4dae94e0cf6216f1dcfc
Source dataset
uspto-grants-2013_12
Patent number
USRE044638E1

Reaction notes

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