Iodoethane → HCID 22996319, compound

Temperature

0 °C

3-Bromo-N-tert-butoxycarbonylaniline (0.82 g, 3.0 mmol) was dissolved in anhydrous DMF (15 ml) and cooled to 0° C. Sodium hydride (0.145 g, 3.6 mmol, 1.2 eq.) was added to the solution. The reaction stirred at 0° C. for 10 minutes then was warmed to room temperature. After 30 minutes at room temperature the reaction was cooled to 0° C. and Ethyl iodide (0.27 ml, 3.3 mmol, 1.1 eq.) was added over ˜1 minute. The reaction was stirred at 0° C. for 5 minutes then was warmed to room temperature. The reaction stirred at room temperature for 22 hours and was then cooled to 0° C. and quenched with a saturated bicarbonate solution and extracted with EtOAc (2 times). The combined organic layers were washed with H2O (5 times) then brine. The organic phase was dried with MgSO4/Na2SO4, filtered and the solvent was removed in vacuo to give 0.93 g of crude product which was used as is. HPLC ret. time=11.83 min. (100%).

1. temperaturethen was warmed to room temperature
2. temperatureAfter 30 minutes at room temperature the reaction was cooled to 0° C.
3. stirringThe reaction was stirred at 0° C. for 5 minutes
4. temperaturethen was warmed to room temperature
5. stirringThe reaction stirred at room temperature for 22 hours
6. temperaturewas then cooled to 0° C.
7. customquenched with a saturated bicarbonate solution
8. extractionextracted with EtOAc (2 times)
9. washThe combined organic layers were washed with H2O (5 times)
10. dry with materialThe organic phase was dried with MgSO4/Na2SO4
11. filtrationfiltered
12. customthe solvent was removed in vacuo

ORD record

ord-c786f98a43c943e69decefabfda79486

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06319946B1