Imidazole → N-{[dimethyl-(4-fluorobenzyl)silyl]methyl}imidazole hydrochloride

HRID 1614553Notes

Reaction equation

HRID 1614553 reaction equation
[Cl:1][CH2:2][Si:3]([CH3:13])([CH3:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.O>C1(C)C(C)=CC=CC=1>[ClH:1].[CH3:12][Si:3]([CH2:2][N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)([CH3:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 15338764Chloromethyl-dimethyl(4-fluorobenzyl)silane

Product 1

HCID 19007260N-{[dimethyl-(4-fluorobenzyl)silyl]methyl}imidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

After dissolving 3.25 g of chloromethyl-dimethyl(4-fluorobenzyl)silane in 10 ml of xylene, 2.55 g of imidazole are added to the solution which is then refluxed for 12 hours. After adding 50 ml of water to the mixture and separating, the organic phase is washed with a total of 100 ml of water in 5 portions. The organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to solvent-free. The pale yellow oily residue is dissolved in 20 ml of ethyl acetate and gaseous hydrogen chloride is introduced to the solution until reaching a pH value of 4 to 5. The precipitated crystalline product name is filtered in two portions at 10° C. and washed with a total of 6 ml of ethyl acetate to give the named compound in a yield of 3.41 g (80%), m.p.: 152°-154° C.

Workup

  1. additionare added to the solution which
  2. temperatureis then refluxed for 12 hours
  3. customseparating
  4. washthe organic phase is washed with a total of 100 ml of water in 5 portions
  5. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate is evaporated to solvent-free
  8. dissolutionThe pale yellow oily residue is dissolved in 20 ml of ethyl acetate
  9. additiongaseous hydrogen chloride is introduced to the solution
  10. filtrationThe precipitated crystalline product name is filtered in two portions at 10° C.
  11. washwashed with a total of 6 ml of ethyl acetate
  12. customto give the named compound in a yield of 3.41 g (80%), m.p.: 152°-154° C.

Sources & evidence

ORD record
ord-c3eb2a7da6274ef6aa7f161ade5291bb
Source dataset
uspto-grants-1993_03
Patent number
US05198446

Reaction notes

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