Acetic Acid → N-[4-chloro-2-(1-cyclohexylmethoxyiminopropyl)phenyl]trifluoromethanesulfonamide

N,N-Dimethylethylenediamine (1.53 mL, 13.18 mmol) was added to a solution of N-(cyclohexylmethoxy)phthalimide (2.33 g, 8.99 mmol) in EtOH (30 mL), and the reaction allowed to stir at RT for 2 hours. Glacial acetic acid (5 mL) was then added to adjust the mixture to ca. pH 4 followed by a solution of N-(4-chloro-2-propionylphenyl)trifluoromethanesulfonamide 22 (1.89 g, 5.99 mmol) in EtOH (10 mL), and the reaction stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum, and the residue dissolved in Et2O (50 mL) and washed with water, brine, dried over MgSO4 and the solvent removed under reduced pressure. The residue was purified by column chromatography (eluting with CH2Cl21PE, 3:4 to 1:3) to afford N-[4-chloro-2-(1-cyclohexylmethoxyiminopropyl)phenyl]trifluoromethanesulfonamide 104 (2.34 g, 91%), as colorless crystals. 1H n.m.r. (400 MHz, CDCl3) δ 12.01, br s, 1H, 7.67, d, J=8.8 Hz, 1H, 7.48, d, J=2.4 Hz, 1H, 7.32, dd, J=2.4 and 8.8 Hz, 1H, 4.02, d, J=6 Hz, 2H, 2.81, q, J=7.6 Hz, 2H, 1.74, m, 6H, 1.27, m, 3H; 1.19, t, J=7.6 Hz, 3H, 1.01, m, 2H. HRMS (M+) 426.0971.

1. stirringthe reaction stirred for 15 hours at RT
2. concentrationThe reaction mixture was concentrated under vacuum
3. dissolutionthe residue dissolved in Et2O (50 mL)
4. washwashed with water, brine
5. dry with materialdried over MgSO4
6. customthe solvent removed under reduced pressure
7. customThe residue was purified by column chromatography (eluting with CH2Cl21PE, 3:4 to 1:3)

ORD record

ord-63a5979470a840e288fa441025c30529

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07906538B2