N-bromobutanimide → HCID 9951199, compound

Participants

Reaction Steps

Dissolve 5.25 g (15.7 mmol) of the product of Example 9i in 100 mL of acetic acid at 0° C. Add 2.79 g (15.7 mmol) of N-bromosuccinimide and 2.61 g (15.6 mmol) of silver acetate, and stir the mixture at ambient temperature for 24 hours. Add 500 mL of 9/1 acetic acid/water and heat to 90° C. for 16 hours. Filter the mixture through Celite, evaporate the solvent, and dissolve the residue in 1 N HCl. Treat the solution with charcoal, filter, and make basic with concentrated NH4OH. Collect the precipitate and wash with water and acetonitrile. Suspend the precipitate in 200 mL of 3/1 methanol/concentrated NH4OH and heat to reflux for 8 hours. Evaporate the mixture, dissolve the residue in 2N HCl, and precipitate with concentrated NH4OH. Collect the precipitate and wash with water and acetonitrile. Triturate the precipitate with boiling methanol, DMF and then again with methanol to provide the title compound.

Provenance & Evidence