Ethanesulfonyl chloride → HCID 67074264, compound

Participants

Reaction Steps

11.7 g 3-(3-aminophenoxy)-5-fluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (24.3 mmol, 1. eq.; containing a minor amount of the regioisomeric 5-(3-aminophenoxy)-3-fluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline) was dissolved in 98 mL pyridine, set under an atmosphere of nitrogen and treated sequentially with 3.4 mL ethyl sulfonyl chloride (36.4 mmol, 1.5 eq.; dissolved in pyridine). The resulting reaction mixture was stirred at rt for 20 h after which LCMC analysis showed final turnover. The reaction mixture was quenched by addition of water and diluted with ethyl acetate and phases were separated. The separated aqueous layer was reextracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 14.8 g of the crude target compound (which contained a minor amount of the regioisomeric N-(3-{3-fluoro-5-[(2-fluoro-4-iodophenyl)amino]-2-nitrophenoxy}-phenyl)ethanesulfonamide) which was used without further purification in the subsequent transformations.

Provenance & Evidence