反应详情

A suspension of 3-iodobenzoic acid (1.24 g, 5.0 mmol) in 15 mL of dichloromethane containing one drop of N,N-dimethylformamide was treated dropwise with oxalyl chloride (0.70 mL, 7.5 mmol). After stirring for 2.5 h at room temperature, the solution was concentrated under reduced pressure to afford a pale orange oil, which was dissolved in 10 mL of dry tetrahydrofuran (THF) and added dropwise to an ice-cold suspension of tert-butyl carbazate (793 mg, 6.0 mmol) and triethylamine (1.10 mL) in 15 mL of dry THF. The resultant mixture was allowed to warm to room temperature overnight, and was then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water, and the organic layer was washed sequentially with 5% aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated aqueous brine, dried (magnesium sulfate), and concentrated under reduced pressure to afford an off-white solid. Trituration with hexanes afforded a white powder, which was suspended in 60 mL of dichloromethane and cooled in an ice-water bath. Trifluoroacetic acid (25 mL) was added dropwise, and the mixture was warmed to room temperature. After 1 h, the solution was concentrated under reduced pressure, and the residue was dissolved in 60 mL of water and was neutralized to pH 8 with 1N aqueous sodium hydroxide solution. The resultant precipitate was collected, washed with water, and dried in vacuo to afford 3-iodobenzhydrazide as a white powder.

1. concentrationthe solution was concentrated under reduced pressure
2. customto afford a pale orange oil, which
3. temperatureto warm to room temperature overnight
4. concentrationwas then concentrated under reduced pressure
5. customThe residue was partitioned between ethyl acetate and water
6. washthe organic layer was washed sequentially with 5% aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated aqueous brine
7. dry with materialdried (magnesium sulfate)
8. concentrationconcentrated under reduced pressure
9. customto afford an off-white solid
10. temperaturecooled in an ice-water bath
11. temperaturethe mixture was warmed to room temperature
12. waitAfter 1 h
13. concentrationthe solution was concentrated under reduced pressure
14. dissolutionthe residue was dissolved in 60 mL of water
15. customThe resultant precipitate was collected
16. washwashed with water
17. customdried in vacuo