N-bromobutanimide → 1-(5-Bromo-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)-benzyl)imidazolidin-2-one

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° C. 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).

1. customquenched with 10% sodium thiosulfate solution (10 mL)
2. additiondiluted with ethyl acetate (200 mL)
3. washwashed with water and brine
4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography

ORD-Eintrag

ord-5637d9f8db2448d2965b25d8de3e3ca7

Quelldatensatz

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08293768B2