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]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)+.).
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