Carbonate Ion → 1-(8-Bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)-5,5-dimethylimidazolidin-2,4-dione

HRID 2386005Notes

Reaction equation

Br[C:2]([CH3:25])([CH3:24])[C:3]([NH:5][C:6](=[O:23])[NH:7][C:8]1[S:9][C:10]2[CH2:16][CH2:15][O:14][C:13]3[CH:17]=[C:18]([Br:21])[CH:19]=[CH:20][C:12]=3[C:11]=2[N:22]=1)=[O:4].C(=O)([O-])[O-]>CN(C)C=O>[Br:21][C:18]1[CH:19]=[CH:20][C:12]2[C:11]3[N:22]=[C:8]([N:7]4[C:2]([CH3:25])([CH3:24])[C:3](=[O:4])[NH:5][C:6]4=[O:23])[S:9][C:10]=3[CH2:16][CH2:15][O:14][C:13]=2[CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1.002 g (2.048 mmol) of 2-bromo-2-methyl-N-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)carbamoylpropanamide and 1.660 g (5.11 mmol) of ccesium carbonate in 100 ml of N,N-Dimethylformamide was stirred at 60° C. for 2 hours. The mixture was filtered, the filtrate concentrated in high vacuum, the residue partitioned between ethyl acetate and water. pH was adjusted to 5 by addition of 5% aq citric acid. The organic extracts were washed with water, brine, dried over MgSO4 and concentrated in vacuum to give 1-(8-Bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)-5,5-dimethylimidazolidin-2,4-dione as an off-white powder which was used in the next steps without further purification. Yield 0.812 g (97%). MS (ESI+): 408.1

Workup

filtrationThe mixture was filtered
concentrationthe filtrate concentrated in high vacuum
customthe residue partitioned between ethyl acetate and water
additionpH was adjusted to 5 by addition of 5% aq citric acid
washThe organic extracts were washed with water, brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuum

Sources & evidence

ORD record: ord-8a4adbab2db84ec79a9ac17786b2a93d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263633B2

Reaction notes

Loading…