2-Bromo-1-(2,4-dichlorophenyl)ethan-1-one → HCID 68585005, compound

HRID 1951785Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[S:12](=[O:14])(=[O:13])[NH:11][C:10](=[O:15])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C([O-])(O)=O.[Na+].Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[Cl:32])=[O:24]>C(#N)C.O>[Cl:32][C:26]1[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:25]=1[C:23](=[O:24])[CH2:22][NH:1][C:2]1[CH:3]=[C:4]([N:8]2[S:12](=[O:14])(=[O:13])[NH:11][C:10](=[O:15])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of 5-(3-amino-phenyl)-1,1-dioxo-[1,2,5]thiadiazolidin-3-one (5 g, 22 mmol) in 37.5 mL of 9:1 v/v acetonitrile-water was added NaHCO3 (4.62 g, 55 mmol). The mixture was stirred at 25° C. while 2-bromo-1-(2,4-dichloro-phenyl)-ethanone (7.1 g, 26.4 mmol) was added. The mixture was stirred for 12-16 hours at 35° C. The mixture was cooled on an ice bath to further precipitate the product, which was then collected by filtration. The filtrate was concentrated under reduced pressure and a second crop of crude product was collected. The combined crude product was washed once with 25 mL water and dried, then washed once with 10 mL methyl tert-butyl ether and dried, to provide 6.36 g (70% yield) of 5-{3-[2-(2,4-dichloro-phenyl)-2-oxo-ethylamino]-phenyl}-1,1-dioxo-[1,2,5]thiadiazolidin-3-one.

Workup

additionwas added
temperatureThe mixture was cooled on an ice bath
customto further precipitate the product, which
filtrationwas then collected by filtration
concentrationThe filtrate was concentrated under reduced pressure
customa second crop of crude product was collected
washwas washed once with 25 mL water
customdried
washwashed once with 10 mL methyl tert-butyl ether
customdried

Sources & evidence

ORD record: ord-b6ba890d56034270a983f5918e1c30d0
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404731B2

Reaction notes

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