4-METHYL-N-(2-METHYL-BENZOYL)-BENZENESULFONAMIDE synthesis
- Product Name:4-METHYL-N-(2-METHYL-BENZOYL)-BENZENESULFONAMIDE
- CAS Number:146448-53-5
- Molecular formula:C15H15NO3S
- Molecular Weight:289.35
Yield:146448-53-5 90%
Reaction Conditions:
Stage #1: ortho-methylbenzoic acidwith oxalyl dichloride;N,N-dimethyl-formamide in tetrahydrofuran at 20;Inert atmosphere;
Stage #2: toluene-4-sulfonamidewith dmap;triethylamine in ethyl acetate;toluene at 55; for 3 h;Inert atmosphere;
Steps:
N-Tosylbenzamides 1c,f; General Procedure (G2)
General procedure: To a round-bottom flask were introduced the carboxylic acid (1equiv) in dry THF (8 mL/mmol), a catalytic amount of DMF and oxalylchloride (2 equiv) under N2. The resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, placed under nitrogen and solubilized in dried toluene (0.8 mL/mmol). This solution was added via a syringe over 15 min to a mixture of p-toluenesulfonamide (1 equiv), Et3N (2.5equiv) and DMAP (0.5 mol%) in EtOAc (2 mL/mmol) under nitrogen. The resulting mixture was stirred for 3 h at 55 °C, cooled to room temperature and quenched with 0.5 M aqueous HCl solution (3mL/mmol). The resulting mixture was extracted with EtOAc (3 times). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography using AcOH/EtOAc/cyclohexane(5:15:85) as eluent.
References:
Babin, Victor;Benoist, Florian;Bouillon, Jean-Philippe;Cailly, Thomas;Dubost, Emmanuelle;Fabis, Frédéric;Hébert, Alexandra;Pigrée, Gilbert [Synthesis,2019,vol. 51,# 23,p. 4393 - 4400]
![[N-(p-Toluenesulfonyl)imino]phenyliodinane](/CAS/GIF/55962-05-5.gif)
