Reaktion #642080

Reaktionsgleichung

4-fluorobenzyl bromide

4-fluorobenzyl bromide

potassium carbonate

4-methyl-2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)thiazole-5-carboxylate

4-fluorobenzyl bromide

potassium carbonate

tetrahydrofuran

→

title compound

Ausbeute 59.0%

ethyl 2-(3-(4-fluorobenzyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-4-methylthiazole-5-carboxylate

Ausbeute 59.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for 3 h
2. 2
   workup.STIRRINGstirred at ambient temperature for 17 h
3. 3
   workup.STIRRINGThe mixture was stirred for an additional 3 h at ambient temperature
4. 4
   Filtrationfiltered
5. 5
   Waschenwashed with tetrahydrofuran
6. 6
   EinengenThe filtrate was concentrated
7. 7
   Sonstigethe residue was purified by column chromatography

Vorschrift

To a 25-mL round bottom flask was added 4-methyl-2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)thiazole-5-carboxylate (0.10 g, 0.33 mmol), tetrahydrofuran (95 mL), 4-fluorobenzyl bromide (0.08 g, 0.43 mmol) and potassium carbonate (0.10 g, 0.73 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 16 h and refluxed for 3 h. The second portion of 4-fluorobenzyl bromide (0.08 g, 0.43 mmol) was added and stirred at ambient temperature for 17 h. The third portion of 4-fluorobenzyl bromide (0.08 g, 0.43 mmol) and second portion of potassium carbonate (0.10 g, 0.73 mmol) were added at ambient temperature. The mixture was stirred for an additional 3 h at ambient temperature, filtered and washed with tetrahydrofuran. The filtrate was concentrated and the residue was purified by column chromatography to afford the title compound as a white solid (0.08 g, 59% yield): mp 192-193° C.; 1H NMR (300 MHz, CDCl3) δ 8.58-8.55 (m, 1H), 7.38-7.31 (m, 2H), 7.26-7.16 (m, 2H), 7.05-6.95 (m, 3H), 5.09 (s, 2H), 4.32 (q, J=7.2 Hz, 2H), 2.76 (s, 3H), 1.36 (t, J=7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 162.8, 157.1, 157.0, 151.9, 131.0, 131.0, 129.5, 129.4, 128.9, 126.3, 124.2, 122.9, 116.8, 116.1, 115.8, 115.0, 108.4, 61.0, 44.5, 17.5, 14.3; MS (ES+) m/z 412.0 (M+1).

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