Lithium Hydroxide → 1301214-58-3

Temperature

50 °C

Methyl 7-chloro-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate (351 mg, 1.55 mmol), 1 M aqueous lithium hydroxide (0.774 mL, 1.55 mmol) and tetrahydrofuran (5 mL) were combined and heated to 50° C. for 2 hours. To the reaction was added 1 M aqueous lithium hydroxide (0.774 mL, 1.55 mmol) and methanol (10 mL) and the reaction was heated to reflux for 6 hours and then allowed to cool to ambient temperature overnight. The reaction solution was concentrated in vacuo to remove the tetrahydrofuran and methanol. The residual aqueous layer was extracted with ethyl acetate (2 mL). To the aqueous layer was added water (2 mL) ethyl acetate (2 mL) and 3 M aqueous hydrochloric acid. A precipitate formed. The mixture was filtered and the solids were washed with water and ethyl acetate. The solids were dried under a stream of nitrogen to give the title compound (296 mg, 90%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (s, 1H) 11.12 (s, 1H) 7.54 (d, J=1.37 Hz, 1H) 7.38 (d, J=1.37 Hz, 1H).

1. temperaturethe reaction was heated
2. temperatureto reflux for 6 hours
3. temperatureto cool to ambient temperature overnight
4. concentrationThe reaction solution was concentrated in vacuo
5. customto remove the tetrahydrofuran and methanol
6. extractionThe residual aqueous layer was extracted with ethyl acetate (2 mL)
7. additionTo the aqueous layer was added water (2 mL) ethyl acetate (2 mL) and 3 M aqueous hydrochloric acid
8. customA precipitate formed
9. filtrationThe mixture was filtered
10. washthe solids were washed with water and ethyl acetate
11. customThe solids were dried under a stream of nitrogen

ORD record

ord-a61ab36b1e23463e8eb894d9b7e949c0

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288405B2