1,1'-Carbonyldiimidazole → HCID 57991956, compound

Temperature

20 °C

3-Fluoro-4-nitrobenzenecarboxylic acid (8.4 g, 45 mmol) and 1,1′-carbonyldiimidazole (10 g, 64 mmol) were mixed in 100 mL DMF. The mixture was stirred at 20° C. for 1 hour. A clear yellow solution formed. To this mixture was added thiosemicarbazide (8.3 g, 91 mmol). The resulting mixture was stirred at 20° C. for 30 minutes. The reaction mixture was concentrated under vacuum to remove almost all the DMF. The remaining residue was treated with 2 N HCl with stirring until the solution reached pH 4. Upon standing, a yellow solid formed. The pure product was obtained as a yellow solid after filtering, washing with water, and drying (8.02 g, 68% yield). LCMS (API-ES) m/z (%): 259.1 (100%, M++H); 1H NMR (400 MHz, DMSO-d6) δ ppm 7.81 (s, 1H) 7.90 (d, J=8.41 Hz, 1H) 7.99 (s, 1H) 8.04 (d, J=11.93 Hz, 1H) 8.28 (t, J=8.02 Hz, 1H) 9.47 (s, 1H) 10.76 (s, 1H).

1. customA clear yellow solution formed
2. stirringThe resulting mixture was stirred at 20° C. for 30 minutes
3. concentrationThe reaction mixture was concentrated under vacuum
4. customto remove almost all the DMF
5. additionThe remaining residue was treated with 2 N HCl
6. stirringwith stirring until the solution
7. customa yellow solid formed
8. customThe pure product was obtained as a yellow solid
9. filtrationafter filtering
10. washwashing with water
11. customdrying (8.02 g, 68% yield)

ORD record

ord-eb226f951f4e49138878f63a58cd0002

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07919504B2