(Trimethylsilyl)imidazole → HCID 178424778, compound

HRID 1761517Notes

Reaction equation

HRID 1761517 reaction equation
C[Si](C)(C)[N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Cl[CH:11]([C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:20])[CH3:12]>C(Cl)(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:12][CH:11]([C:7]1[N:3]=[CH:4][NH:5][CH:6]=1)[C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:20]

Participants

5

Reactant 2

HCID 28925(Trimethylsilyl)imidazoleHCID 156377741-Chloro-1-(2,6-dimethylphenyl)ethane

Product 1

HCID 178424778HCID 178424778, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6212ChloroformSolvent2×

Procedure

To a mixture of N-(trimethylsilyl)imidazole (1.4 g) and titanium tetrachloride (1.6 ml) in dry chloroform (20 ml) a solution of 1-chloro-1-(2,6-dimethylphenyl)ethane (1.7 g) in dry chloroform (10 ml) was added. After stirring for 5 h at room temperature the product mixture was poured onto water, washed with ether and neutralized with sodium hydrogen carbonate. Filtration and extraction with methylene chloride gave 4-[(α-methyl)-2,6-dimethylbenzyl]imidazole, yield 33%.

Workup

  1. additionwas added
  2. additionwas poured onto water
  3. washwashed with ether and neutralized with sodium hydrogen carbonate
  4. filtrationFiltration and extraction with methylene chloride

Sources & evidence

ORD record
ord-68161d12b8684ce0b2becfe71de8cae6
Source dataset
uspto-grants-1989_05
Patent number
US04826864

Reaction notes

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