Ammonia → 2-(2,6-diethyl-benzyl)-1H-imidazole

HRID 254528Notes

Reaction equation

HRID 254528 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([C:13]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH3:26])[C:14]=1[CH2:15][C:16]1[NH:17][CH2:18][CH2:19][N:20]=1)[CH3:12].N>ClCCl.C(N(CC)CC)C>[CH2:11]([C:13]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH3:26])[C:14]=1[CH2:15][C:16]1[NH:17][CH:18]=[CH:19][N:20]=1)[CH3:12]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 247817142-(2,6-diethyl-benzyl)-4,5-dihydro-1H-imidazole

Product 1

HCID 247818692-(2,6-diethyl-benzyl)-1H-imidazoleYield 73.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1.08 g (14 mmol) dimethylsulfoxide in 100 ml dichloromethane cooled to −78° C. was added a solution of 1.82 g (14 mmol) oxalyl chloride in 7 ml dichloromethane. The mixture was stirred for 50 minutes at −78° C. and then a solution of 0.620 g (3 mmol) 2-(2,6-diethyl-benzyl)-4,5-dihydro-1H-imidazole in 80 ml dichloromethane was added and stirring continued at −78° C. for 90 minutes. Then 2.90 g triethylamine were added and the reaction mixture warmed to ambient temperature and stirring continued for 2 hours. Concentrated ammonia was added and the reaction mixture extracted with ethyl acetate, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. Purification on silica gel by flash-chromatography with a heptane/ethyl acetate gradient followed by trituration of residue of the collected and evaporated fractions in tert.-butyl methyl ether provided 0.475 g 2-(2,6-diethyl-benzyl)-1H-imidazole as colourless solid: MS (ISP): 215.2 ((M+H)+.).

Workup

  1. stirringstirring
  2. waitcontinued at −78° C. for 90 minutes
  3. temperaturethe reaction mixture warmed to ambient temperature
  4. stirringstirring
  5. waitcontinued for 2 hours
  6. extractionthe reaction mixture extracted with ethyl acetate
  7. washthe combined extracts washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customPurification on silica gel by flash-chromatography with a heptane/ethyl acetate gradient
  12. customcollected
  13. customevaporated fractions in tert.-butyl methyl ether

Sources & evidence

ORD record
ord-97c82217ee7a43a8bac9a9403bb0d0d7
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

Loading…