Triethylamine → HCID 11949830, compound

Participants

Reaction Steps

To a solution of 1-(4-aminobenzyl)-3-(4-tert-butylbenzyl)-imidazolidin-2-one (F) (410 mg, 1.22 mmol) and triethylamine (0.2 mL, 1.44 mmol) in abs. THF there was added a solution of methanesulphonyl chloride (0.12 mL, 1.56 mmol) in 0.8 mL of abs. THF within a period of 20 min. The reaction mixture was stirred over a period of 15 h at RT, sat. NaHCO3 solution (10 mL) was added, and the mixture was stirred for 30 min. H2O (30 mL) was added and the mixture was extracted with EtOAc (3×20 mL). The combined organic phases were washed with sat. NaCl solution, dried over Na2SO4, and the solvent was removed in vacuo. Following purification, by column chromatography, of the residue (SiO2, EtOAc/cyclohexane 2:1), there were obtained the desired product N-{4-[3-(4-tert-butylbenzyl)-2-oxoimidazolidin-1-ylmethyl]phenyl}methanesulfonamide (4) (70 mg, 14% of theory, mp: 166-168° C.) and N-{4-[3-(4-tert-butylbenzyl)-2-oxoimidazolidin-1-ylmethyl]phenyl}-N,N-bis(methanesulfonyl)imide (G) (160 mg, mp: 184-187° C.).

Provenance & Evidence