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ChemicalBook CAS DataBase List 2H-Benzimidazol-2-one,4-fluoro-1,3-dihydro-(9CI)
256519-10-5

2H-Benzimidazol-2-one,4-fluoro-1,3-dihydro-(9CI) synthesis

2synthesis methods
-

Yield:256519-10-5 97%

Reaction Conditions:

in tetrahydrofuran at 20 - 50;

Steps:

2.09.a; 2.10.a

a) 3-Fluorobenzene-1,2-diamine (0.600 g, 4.76 mmol) was dissolved in THF (14.82 ml) and 1,1'-carbonyldiimidazole (0.848 g, 5.23 mmol) was added at RT. The reaction mixture was stirred overnight at RT and then heated for 24 hours at 50° C. The mixture was cooled to RT and ammonia in MeOH (1.5 ml) was added and the mixture stirred for 30 minutes. The mixture was dilued with water (40 ml) and the resultant brown solid was collected by filtration, washed with water and then dried in vacuo to afford 4-fluoro-1H-benzo[d]imidazol-2(3H)-one (0.700 g, 97%) which was used in the next step without further purification; 1H NMR (400 MHz, DMSO-d6) 6.81 (2H, ddd), 6.88-6.95 (1H, m), 10.82 (1H, s), 11.08 (1H, s); m/z: (ES-) M-H-, 151.19.

References:

US2011/306613,2011,A1 Location in patent:Page/Page column 31