Imidazole → (Trimethylsilyl)imidazole

HRID 435198

Reaction equation

HRID 435198 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][Si](C)(C)C.[NH:10]1[CH:14]=[CH:13]N=[CH:11]1>S1(C2C(=CC=CC=2)C(=O)N1)(=O)=O>[CH3:1][Si:2]([CH3:9])([CH3:8])[N:3]1[CH:13]=[CH:14][N:10]=[CH:11]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 13838Hexamethyldisilazane2×

Product 1

HCID 28925(Trimethylsilyl)imidazoleYield 105.8%

Reagents, catalysts & solvents 1

HCID 5143SaccharinCatalyst

Conditions

Temperature
100 °C

Procedure

31.5 ml (0.15 mole) of hexamethyldisilazane were added dropwise over the course of 45 minutes to 13.62 g (0.2 mole) of imidazole and 28 mg (0.15 mmoles) of saccharin heated to 100° C. and during this addition, the bath temperature was raised from 100° to 140° C. After addition of the hexamethyldisilazane, the mixture was stirred for 30 minutes at a bath temperature of 140° C. Excess hexamethyldisilazane was evaporated under reduced pressure and the residue was vacuum distilled to obtain 22,25 g (79.5%) of N-trimethylsilylimidazole boiling at 103°-105° C. at 22 mm Hg and nD 23.5°=1.4740.

Workup

  1. temperaturethe bath temperature was raised from 100° to 140° C
  2. customExcess hexamethyldisilazane was evaporated under reduced pressure
  3. distillationdistilled

Sources & evidence

ORD record
ord-5c4efbded4fa4d69b4330163dbb5b738
Source dataset
uspto-grants-1983_08
Patent number
US04400509

Linked notes

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