Tetrahydrofuran → HCID 19874945, compound

Participants

Reaction Steps

2.0 g (6.36 mmol) of the N-morpholinosulfonylphenylaniline was added to ice-cold SOCl2 (4 mL), and the reaction mixture was gradually warmed to room temperature and stirred overnight at room temperature. The solvent was evaporated under rotary evaporator. Toluene (10 mL) was added and the solution was evaporated. This process was repeated twice to remove any excess HCl(g). This was dissolved in THF (20 mL) and added slowly to a solution of 2,6-diisopropylaniline (1.0 g, 5.72 mmol) and Et3N (1.3 mL, 12.7 mmol) in THF (20 mL). The solution was stirred overnight at room temperature to complete the reaction. THF was evaporated, the residue was dissolved in CH2Cl2, and the solution was washed successively with 1N HCl, saturated NaHCO3, and brine. The solution was dried over anhydrous MgSO4, stripped and chromatographed (SiO2, 0-2% MeOH/CHCl3) to give 3 g (85%) of the desired product.

Provenance & Evidence