Chlorosulfonic acid → HCID 86758935, compound

Participants

Reaction Conditions

Reaction Steps

(R)-N-{2,3-Dichlorophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 74) (5.0 g, 16.6 mmol) was added in portions to cooled (0° C.) chlorosulphonic acid (5.3 ml, 81 mmol) over 15 mins and then the mixture was heated to 85° C. for 4.5 hours. The reaction mixture was cooled in an ice bath and then poured slowly onto a stirred ice-water mixture (60 ml). The mixture was extracted with DCM (2×75 ml), the DCM washed with brine, dried and evaporated. The residue was chromatographed on silica with 20% EtOAc in hexane as eluent to give the title compound as a solid (3.0 g, 7.5 mmol). NMR (CDCl3): 1.8 (s, 3H), 3.4 (s, 1H), 8.15 (d, 1H), 8.65 (d, 1H) and 9.55 (brs, 1H); m/z 400.

Provenance & Evidence