Diethylamine → N,N-Diethyl-3-iodobenzamide

3-Iodobenzoic acid (55.5 g, 0.224 mol) was dissolved in tetrahydrofuran (220 mL) and oxalyl chloride (22 mL, 0.252 mol). Catalytic dimethylformamide (4 drops) was added, the solution was stirred at room temperature for 1 hour, and the solvent was removed under vacuum. The residue was dissolved in 220 mL petroleum ether (35°-60° C. boiling range) and cooled to 0° C. in an ice bath. Diethylamine (55 mL, 0.532 mol) was then added dropwise over 15 minutes. The reaction mixture was stirred an additional 15 minutes in the ice bath, then diluted with ethyl acetate (100 mL) and washed with saturated sodium chloride solution (50 mL). The organic layer was separated, dried over magnesium sulfate, and concentrated in vacuo to approximately half of the original volume. The solution was then filtered through a small pad of silica gel, using ethyl acetate to was the pad. All volatiles were removed in vacuo, and the product was dried under high vacuum to give 65.69 g (97%) of N,N-diethyl-3-iodobenzamide as an amber oil.

1. customthe solvent was removed under vacuum
2. dissolutionThe residue was dissolved in 220 mL petroleum ether (35°-60° C. boiling range)
3. temperaturecooled to 0° C. in an ice bath
4. washwashed with saturated sodium chloride solution (50 mL)
5. customThe organic layer was separated
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated in vacuo to approximately half of the original volume
8. filtrationThe solution was then filtered through a small pad of silica gel
9. customAll volatiles were removed in vacuo
10. customthe product was dried under high vacuum

ORD record

ord-85a0face663d4c038d1572965fe2425d

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05574159