1,3-Dibromo-5,5-dimethylhydantoin → HCID 58529885, compound

Participants

Reaction Steps

The product from step 1 (1.54 g, 6.4 mmol) was dissolved in 18 mL of 1:1 DMF:THF. The mixture was cooled to −20° C. (internal temperature) and 1,3-dibromo-5,5-dimethylhydantoin (0.92 g, 3.2 mmol) was added in 4 equal portions over 40 minutes. The mixture was stirred for an additional 1 hour during which the internal temp rose to −5° C. A solid mass formed, which was diluted with a mixture of 15 mL of 2M Na2CO3, 10 mL of sat. Na2SO3 and 60 mL of water and the mixture was stirred for an additional 30 minutes. The solid was collected by filtration, washed with water and dried in a vacuum oven at 40° C. to give 1.96 g (95%) of the title compound as a tan solid. 1H-NMR (DMSO-d6) 8.10 (bs, 1H), 7.94 (s, 2H), 7.86 (d, 1H), 7.40 (t, 1H), 7.29 (d, 1H), 7.17 (s, 1H), 6.84 (bs, 1H), 5.22 (t, 1H), 4.56 (d, 2H); LC-MS [M+H]+=319.3, 321.1, RT=2.29 min.

Provenance & Evidence