1,2-Dichloroethane → 5-Iodo-2-methoxybenzamide

5-iodo-2-methoxybenzoic acid (1.01 g, 3.63 mmol) was dissolved in DMF (8.0 ml) and EDC (0.86 g, 4.5 mmol), HOAt (0.59 g, 4.3 mmol), ammonium chloride (0.79 g, 14.8 mmol), and iPr2NEt (2.0 ml, 11.5 mmol) were added. The reaction was stirred at room temperature under nitrogen overnight, and then poured into water (40 ml), resulting in the formation of a precipitate. The suspension was filtered and the solid was collected. The filtrate was extracted with EtOAc (3×25 ml), and the organic extracts were combined, dried over sodium sulfate, filtered, combined with the filtered solid, and concentrated. The crude was dissolved in DMF (ca. 10 ml) and poured into water (60 ml). This was then cooled in an ice water bath, and filtered, and the solid was collected and dried in vacuo to give title compound (0.38 g, 38%). MS (ESI pos. ion) m/z: 278 (M+H). Calc'd Exact Mass for C8H8INO2: 277.

1. customresulting in the formation of a precipitate
2. filtrationThe suspension was filtered
3. customthe solid was collected
4. extractionThe filtrate was extracted with EtOAc (3×25 ml)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. dissolutionThe crude was dissolved in DMF (ca. 10 ml)
9. additionpoured into water (60 ml)
10. temperatureThis was then cooled in an ice water bath
11. filtrationfiltered
12. customthe solid was collected
13. customdried in vacuo

ORD record

ord-c64210a9691a43318d9d47c4e37cef44

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017601B2