Sodium Azide → 4-Azido-3-iodobenzoic acid

To a solution of methyl 4-amino-3-iodobenzoate (10.0 g, 36.1 mmol) in THF (200 ml), 1M hydrochloric acid (75 ml) and water (300 ml) was added sodium nitrite (2.5 g, 36.1 mmol) under ice-cooling, and the mixture was stirred for 30 min. Sodium azide (2.5 g, 36.1 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 6 hr and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was dissolved in methanol (370 ml), 8M aqueous sodium hydroxide solution (20 ml) and water (30 ml), and the reaction mixture was stirred at room temperature for 18 hr. Methanol was evaporated under reduced pressure, and the obtained residual aqueous solution was acidified (pH<3) with 6M hydrochloric acid and stood still at 0° C. The precipitate was collected by filtration, washed with water and dried to give the title compound as a pale-yellow powder (9.05 g, 95%).

1. temperaturecooling
2. stirringthe mixture was stirred at room temperature for 6 hr
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. dissolutionThe residue was dissolved in methanol (370 ml)
8. stirring8M aqueous sodium hydroxide solution (20 ml) and water (30 ml), and the reaction mixture was stirred at room temperature for 18 hr
9. customMethanol was evaporated under reduced pressure
10. customstood still at 0° C
11. filtrationThe precipitate was collected by filtration
12. washwashed with water
13. customdried

ORD record

ord-6b551be7d680409abb0821b1d9e42bb2

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803822B2