N-bromobutanimide → 1-(5-Bromo-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)-benzyl)imidazolidin-2-one
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[C:8]2=[O:23])[S:5][CH:6]=1.[Br:24]N1C(=O)CCC1=O>C(#N)C>[Br:24][C:6]1[S:5][C:4]([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=3)[C:8]2=[O:23])=[N:3][C:2]=1[CH3:1]Participants
Procedure
To a solution of 1-(4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)-imidazolidin-2-one (1.40 g, 4.10 mmol) in acetonitrile (40 mL) was added N-bromosuccinimide (0.73 g, 4.10 mmol). The reaction mixture was stirred at 0 for 1 h, quenched with 10% sodium thiosulfate solution (10 mL), diluted with ethyl acetate (200 mL), washed with water and brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a colorless solid in 69% yield (1.20 g): mp 107-108° C. (ethyl acetate/hexanes): 1H NMR (300 MHz, CDCl3) δ 7.59 (d, J=7.8 Hz, 2H), 7.39 (d, J=7.8 Hz, 2H), 4.51 (s, 2H), 4.08-3.99 (m, 2H), 3.47-3.41 (m, 2H), 2.25 (s, 3H): MS (ES+) m/z 420.1 (M+1), 422.1 (M+1).
Workup
- customquenched with 10% sodium thiosulfate solution (10 mL)
- additiondiluted with ethyl acetate (200 mL)
- washwashed with water and brine
- dry with materialThe organic solution was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-228da11f97324173a109a49f1b37b0fb
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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