Sulfuric Acid → HCID 118093608, compound

Participants

Reaction Conditions

Reaction Steps

Add sulfuric acid (2.5 mL, 44.9 mmol) to a suspension of 1-(4-aminophenyl)-N-methyl-methanesulfonamide (7.5 g, 37.5 mmol) in water (56.2 mL) and chill the reaction mixture to 0° C. Slowly, drop wise add a solution of sodium nitrite (2.8 g; 41.2 mmol) in water (37.5 mL) to this slurry. Stir the resulting mixture at 0° C. for 20 m, then remove the ice bath and heat the reaction at 100° C. Cool the mixture to room temperature. Quench the reaction with an excess of water and extract with EtOAc. Combine the EtOAc extracts, wash the extracts with brine; dry over MgSO4; filter; and concentrate the filtrate under reduced pressure to yield the title compound as an orange solid (6.2 g, 66%). MS (m/z): 219 (M+H2O).

Provenance & Evidence