反应详情

温度

90 °C

A mixture of 2,6-dichlorobenzothiazole (1.0 g, 4.9 mmol) and 2-fluoro-4-iodoaniline (2.32 g, 9.8 mmol) in 20 mL BuOH was stirred at 90° C., and then HCl (4 M in dioxane, 1.0 mL) was added. The reaction mixture was stirred with heating at 90° C. overnight, under argon. NMR analysis then showed little 2,6-dichlorobenzothiazole remaining. After BuOH was removed by rotary evaporation, EtOAc (100 mL) and 1 N aqueous HCl (100 mL) were added. The organic layer was separated and washed with 1 N aqueous HCl (100 mL), saturated Na2O2S3 solution (50 mL), water (100 mL), and then dried over Na2SO4. Removal of solvent under reduced pressure afforded a residue, which was triturated with EtOAc (10 mL) and hexanes (40 mL). The solid was filtered and dried in vacuo to a constant weight, to afford the desired product as a light purple solid (0.75 g, 38%). 1H NMR (DMSO-d6) δ 10.45 (s, 1H), 8.35 (t, 1H), 7.95 (s, 1H), 7.70 (d, 1H), 7.58 (d, 2H), 7.30 (d, 1H).

1. stirringThe reaction mixture was stirred
2. temperaturewith heating at 90° C. overnight, under argon
3. customAfter BuOH was removed by rotary evaporation, EtOAc (100 mL) and 1 N aqueous HCl (100 mL)
4. additionwere added
5. customThe organic layer was separated
6. washwashed with 1 N aqueous HCl (100 mL), saturated Na2O2S3 solution (50 mL), water (100 mL)
7. dry with materialdried over Na2SO4
8. customRemoval of solvent under reduced pressure
9. customafforded a residue, which
10. customwas triturated with EtOAc (10 mL) and hexanes (40 mL)
11. filtrationThe solid was filtered
12. customdried in vacuo to a constant weight