Imidazole → (Trimethylsilyl)imidazole

HRID 2279433Notes

Reaction equation

HRID 2279433 reaction equation
[CH3:1][Si:2]([NH:5][Si](C)(C)C)([CH3:4])[CH3:3].[NH:10]1[CH:14]=[CH:13]N=[CH:11]1>C1(C)C=CC=CC=1>[CH3:1][Si:2]([CH3:4])([CH3:3])[N:5]1[CH:13]=[CH:14][N:10]=[CH:11]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 13838Hexamethyldisilazane

Product 1

HCID 28925(Trimethylsilyl)imidazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

HMDS (11.46 mL, 0.055 mol, 1.5 eq) was added dropwise over 20 min to a solution of imidazole (5.0 g, 0.074 mol, 2 eq) in 150 ml of toluene under argon, then the reaction mixture heated to reflux for 3 h. The reaction mixture was then concentrated to dryness under reduced pressure. Distillation of the residue gave AA2-2 as a colorless oil in 85%. For best results, this product should be stored at 0° C. under argon.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 3 h
  3. concentrationThe reaction mixture was then concentrated to dryness under reduced pressure
  4. distillationDistillation of the residue
  5. customgave AA2-2 as a colorless oil in 85%
  6. customFor best results
  7. customshould be stored at 0° C. under argon

Sources & evidence

ORD record
ord-80204c62d78c4ab599f21066d441f4ae
Source dataset
uspto-grants-2015_09
Patent number
US09133235B2

Reaction notes

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