Iodoethane → 2-sec-butyl-4-methoxy-N,N-diethylbenzamide

To a mixture of diisopropylamine (40.7 mL, 290 mmol) in THF (800 mL) at -78° C. was added n-BuLi (100 ML, 255 mmol, 2.15M). The mixture was stirred for 1/4 hour, then 2-ethyl-4-methoxy-N,N-diethylbenzamide (235.3 g) in THF (300 mL) was added at -78° C. The mixture was stirred at -78° C. for 2.5 hours, then at 0° C. for 1 hour, and then ethyliodide (23.2 mL) in THF (150 mL) was added over 10 minutes at -78° C. The reaction mixture was stirred for about 1 hour, quenched with saturated NH4Cl (100 mL) and the solvent was removed in vacuo. Ether (500 mL) was added to the residue, the ether layer was washed with saturated NaHCO3 (50 mL), 1N HCl (50 mL), water, then brine, and then the ether layer was dried over Na2SO4 and the solvent was removed in vacuo. The residue was purified by distillation under high vacuum (2 mm Hg) to afford 46.6 g (76%) of 2-sec-butyl-4-methoxy-N,N-diethylbenzamide.

1. stirringThe mixture was stirred at -78° C. for 2.5 hours
2. stirringThe reaction mixture was stirred for about 1 hour
3. customquenched with saturated NH4Cl (100 mL)
4. customthe solvent was removed in vacuo
5. additionEther (500 mL) was added to the residue
6. washthe ether layer was washed with saturated NaHCO3 (50 mL), 1N HCl (50 mL), water
7. dry with materialbrine, and then the ether layer was dried over Na2SO4
8. customthe solvent was removed in vacuo
9. distillationThe residue was purified by distillation under high vacuum (2 mm Hg)

ORD record

ord-7c66508f20e046abbe4c2565e85d7212

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05378720