4-Toluenesulfonyl chloride → HCID 86751730, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3,6,14,17,23,24-hexaazatricyclo-[17.3.1.18,12 ]tetracosa-1(23),8,10,12(24),19,21-hexaene (460 mg, 1.41 mmol) (G L Rothermel, L Miao, A L Hill, L C Jackels, Inorg Chem, 1992, 31, 4854) and triethylamine (0.60 ml, 4.233 mmol) at 0° C. in 40 ml of CH2 Cl2 under an argon atmosphere was added a solution of p-toluenesulphonyl chloride (804 mg, 4.233 mmol) in 10 ml of CH2 Cl2 dropwise over 15 min. The solution was stirred at 0° C. for 30 minutes and warmed to room temperature and stirred a further 4 hours. The reaction mixture was quenched with saturated NH4Cl (10 ml), the aqueous phase extracted with CH2Cl2, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel using 5% MeOH in CH2Cl2 as eluent giving 3,6,14-tris(p-toluenesulphonyl)-3,6,14,17,23,24-hexaaza-tricyclo[17.3.1.18,12 ]tetracosa-1(23),8,10,12(24),19,21-hexaene (300 mg, 27%) as a white solid.

Provenance & Evidence