1,3-Dibromo-5,5-dimethylhydantoin → HCID 58529693, compound

HRID 1972753Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]2[N:25]3[C:20]([C:21]([NH2:26])=[N:22][CH:23]=[N:24]3)=[CH:19][CH:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:27]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]2[N:25]3[C:20]([C:21]([NH2:26])=[N:22][CH:23]=[N:24]3)=[C:19]([Br:27])[CH:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -20 °C

Procedure

The product of step 6 (3.59 g, 10.22 mmoL) was dissolved in 40 mL of DMF and cooled in an Ice/isopropanol/dry ice bath to −20° C. and 1,3-dibromo-5,5-dimethylhydantoin (1.46 g, 5.11 mmol) was added in 4 equal portions 15 minutes apart. The mixture was stirred for 10 minutes past the last addition and quenched by addition to a mixture of ice (400 g), saturated, aqueous Na2SO3 (20 mL) and 2M aq. Na2CO3 (20 mL) and the mixture was allowed to reach rt and vigorously stirred for 30 minutes. The solid was collected by filtration dried in a vacuum oven until a constant weight was obtained. The title compound (4.28 g) was obtained as a freely flowing solid. 1H NMR (300 MHz, CD3OD) δ 7.83 (s, 1H), 7.40-7.25 (m, 5H), 6.66 (s, 1H), 5.06 (bs, 2H), 4.19 (d, 1H), 3.92 (m, 1H), 3.22 (m, 1H), 3.12-2.83 (m, 3H), 1.99, (m, 1H), 1.78-1.62 (m, 2H), 1.48 (m, 1H). ES-MS m/z 430.1, 432.0 [M+H]+, HPLC RT (min) 2.98.

Workup

customquenched by addition to a mixture of ice (400 g)
customto reach rt
stirringvigorously stirred for 30 minutes
filtrationThe solid was collected by filtration
customdried in a vacuum oven until a constant weight
customwas obtained

Sources & evidence

ORD record: ord-5e7b25d116e9492c93759dbfa23dc2c3
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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