Triethylamine → N-(2-Chloro-4-methylphenyl)methanesulfonamide

A solution of 2-chloro-4-methylaniline (5.00 g) and triethylamine (3.57 g) in dichloromethane (100 ml) was cooled to 0° C. Methanesulphonyl chloride (4.04 g) was added dropwise and the mixture stirred at ambient temperature overnight. The mixture was then washed with 2N aqueous hydrochloric acid solution (50 ml) and the solvent removed by evaporation. The residue was dissolved in ethyl acetate (75 ml) extracted with 2N aqueous sodium hydroxide solution (2×50 ml). The aqueous phase was acidified with 2N aqueous hydrochloric acid solution and extracted with ethyl acetate (2×75 ml). This was subsequently dried (MgSO4) and the solvent evaporated. Thus was obtained N-(2-chloro-4-methylphenyl)methanesulphonamide (2.5 g, 32%). NMR Spectrum 2.33 (3H, s), 2.97 (3H, s), 6.6 (1H, s), 7.10 (1H, d), 7.25 (1H, s), 7.52 (1H, d).

1. washThe mixture was then washed with 2N aqueous hydrochloric acid solution (50 ml)
2. customthe solvent removed by evaporation
3. dissolutionThe residue was dissolved in ethyl acetate (75 ml)
4. extractionextracted with 2N aqueous sodium hydroxide solution (2×50 ml)
5. extractionextracted with ethyl acetate (2×75 ml)
6. dry with materialThis was subsequently dried (MgSO4)
7. customthe solvent evaporated

ORD record

ord-0533d51cf27c41d48af9351d24ce8f58

Source dataset

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05258399