Imidazole → HCID 66642939, compound

HRID 1170978Notes

Reaction equation

HRID 1170978 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].N1C=CN=C1.[CH:16]([Si:19](Cl)([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])([CH3:18])[CH3:17]>C(Cl)Cl>[CH3:10][C:3]1[CH:4]=[C:5]([O:9][Si:19]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:16]([CH3:18])[CH3:17])[CH:6]=[C:7]([CH3:8])[C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 765434-Amino-3,5-dimethylphenolHCID 139400Triisopropylsilyl chloride

Product 1

HCID 66642939HCID 66642939, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-amino-3,5-dimethylphenol (5.0 g, 36.46 mmol, Fieser, L. F. Organic Syntheses, Collect Vol II, 1943, 39), imidazole (6.21 g, 77.37 mmol) and triisopropylsilyl chloride (7.70 g, 40.1 mmol) in CH2Cl2 (80 mL) was stirred at room temperature for 1 h. The reaction mixture was diluted with CH2Cl2 (100.0 mL) and washed with water and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:19) to afford 2,6-dimethyl-4-triisopropylsilanyloxyphenylamine (8.46 g, 79%): 1H NMR (300 MHz, CDCl3): δ 6.57 (s, 2 H), 2.19 (s, 6 H), 1.23 (m, 3 H), 1.12 (m, 18 H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:9); Rf=0.51.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate-hexanes (1:19)

Sources & evidence

ORD record
ord-e2bebae423004c11ad2d5eca0f3dfe96
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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