3-Bromo-1,1,1-trifluoro-2-propanone → HCID 15908406, compound

HRID 2086648Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[CH:16][CH:15]=2)=[NH:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)(O)[O-].[Na+].Br[CH2:31][C:32](=O)[C:33]([F:36])([F:35])[F:34]>CC(O)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH:31]=[C:32]([C:33]([F:36])([F:35])[F:34])[N:13]=[C:12]2[C:14]2[CH:19]=[CH:18][C:17]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[CH:16][CH:15]=2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of N-[4-(methylsulfonyl)phenyl]-4-(2-thienyl)benzenecarboximidamide (0.7 g, 1.96 mmol) and sodium bicarbonate (0.33 g, 3.93 mmol) in 2-propanol (30 mL) was added 3-bromo-1,1,1-trifluoroacetone (0.449 g, 2.35 mmol). After the reaction mixture was heated to 80° C. for 21 hours, the solvent was removed. The residue was redissolved in CH2Cl2 (50 mL) and washed with water (30 mL×2). The organic fractions were combined, dried over Na2SO4, filtered, and concentrated in vacuo. The crude mixture was purified by flash chromatography eluting with hexane/ethyl acetate (2/1) to give the subtitle compound (0.351 g, 30.1% yield, via 2 steps).

Workup

customthe solvent was removed
dissolutionThe residue was redissolved in CH2Cl2 (50 mL)
washwashed with water (30 mL×2)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude mixture was purified by flash chromatography
washeluting with hexane/ethyl acetate (2/1)

Sources & evidence

ORD record: ord-59fd872876db43499bcd49f845842318
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727238B2

Reaction notes

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