Tetrahydrofuran → HCID 67151220, compound

Temperature

60 °C

3,4-diamino-5-chlorobenzoate (from acid preparation 1, 100 mg, 0.50 mmol) and carbonyl diimidazole (89 mg, 0.55 mmol) were combined in tetrahydrofuran (2 mL) and stirred for 16 hours. The reaction solution was heated to 60° C. for 3 hours. To the reaction was added carbonyl diimidazole (81 mg, 0.50 mmol) and the reaction was continued at 60° C. for two hours. The reaction was allowed to cool to room temperature and stirred for 16 hours. A precipitate formed. The mixture was filtered. The filtrate was concentrated in vacuo and the residue was slurried in ethyl acetate. The slurry was filtered on the same filter as the original filtration. The collected solids were washed with a portion on ethyl acetate and then dried under a stream of nitrogen to give methyl 7-chloro-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate as a white solid (93 mg, 82%), 1H NMR (400 MHz, DMSO-d6) δ ppm 11.60 (br. s., 1H) 11.16 (s, 1H) 7.55 (d, J=1.37 Hz, 1H) 7.38 (d, J=1.56 Hz, 1H) 3.80 (s, 3H).

1. waitthe reaction was continued at 60° C. for two hours
2. temperatureto cool to room temperature
3. stirringstirred for 16 hours
4. customA precipitate formed
5. filtrationThe mixture was filtered
6. concentrationThe filtrate was concentrated in vacuo
7. filtrationThe slurry was filtered on the
8. filtrationsame filter as the original filtration
9. washThe collected solids were washed with a portion on ethyl acetate
10. customdried under a stream of nitrogen

ORD record

ord-b9325348df1d4963bf665e5e017a949a

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507681B2