Toluene → HCID 11949998, compound

Participants

Reaction Steps

Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetan-2,4-disulfide) (640 mg, 1.58 mmol) was added to a solution of N-{4-[3-(4-tert-butylbenzyl)-2-oxoimidazolidin-1-ylmethyl]phenyl}methanesulfonamide (4) (1008 mg, 2.63 mmol) in abs. toluene (30 mL). The reaction mixture was heated to the boil over a period of 5 h. The reaction mixture was then stirred overnight. Water (40 mL) was added and the mixture was extracted with chloroform (3×30 mL). The combined organic phases were washed with H2O (2×20 mL), dried over Na2SO4, and the solvent was removed in vacuo. Following purification of the residue by means of column chromatography (SiO2 (150 g); 1000 mL cyclohexane/EtOAc 4:1), the desired product N-{4-[3-(4-tert-butylbenzyl)-2-thioxoimidazolidinylmethyl]phenyl}methanesulfonamide (1) (545 mg, 52% of theory) was obtained.

Provenance & Evidence