1,1'-Carbonyldiimidazole → HCID 58963166, compound

Participants

Reaction Steps

2-(4-Cyanophenylamino)-2-(7-ethyl-3-methylbenzofuran-5-yl)acetic acid 6 (5.45 g, 16.4 mmoles), carbonyldiimidazole (CDI, 5.28 g 32.6 mmoles) were combined under a nitrogen atmosphere and THF (50 ml) added. The reaction was stirred for 1 h. Sulfamide (4.7 g, 49 mmoles) was added to the reaction followed by drop wise addition of 1,8-diazabiocyclo[5.4.0]undec-7-ene (DBU, 7.3 ml, 49 mmoles). The reaction was then stirred an additional 2 hours at room temperature and the solvent removed in vacuo. The residue was taken up in ethyl acetate (ca. 150 ml) and washed with aqueous 2 N HCl. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to a yellow foam. The crude product was then purified on a silica flash column eluted with 40% ethyl acetate/60% hexane to provide 2-(4-cyanophenylamino)-2-(7-ethyl-3-methylbenzofuran-5-yl)acetylsulfamide 7 (4.7 g).

Provenance & Evidence