Sodium Acetate → N-{4-chloro-2-[1-(4-chlorophenoxyimino)butyl]phenyl}trifluoromethanesulfonamide

HRID 602619Notes

Reaction equation

HRID 602619 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[C:4]([C:16](=O)[C:17]([CH3:20])(C)C)[CH:3]=1.Cl.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][NH2:31])=[CH:26][CH:25]=1.[CH3:32]C([O-])=O.[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11])=[C:4]([C:16](=[N:31][O:30][C:27]2[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=2)[CH2:17][CH2:20][CH3:32])[CH:3]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 20445467O-(4-chlorophenyl)hydroxylamine hydrochlorideHCID 67270985N-[4-chloro-2-(2,2-dimethylpropionyl)phenyl]trifluoromethanesulfonamide

Product 1

HCID 73021830N-{4-chloro-2-[1-(4-chlorophenoxyimino)butyl]phenyl}trifluoromethanesulfonamideYield 10.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-[4-chloro-2-(2,2-dimethylpropionyl)phenyl]trifluoromethanesulfonamide 29C (300 mg, 0.87 mmol), O-(4-chlorophenyl)hydroxylamine hydrochloride (173 mg, 0.96 mmol) and anhydrous NaOAc (80 mg, 0.96 mmol) in EtOH (20 mL) was stirred for 40 hours at RT. The reaction mixture was concentrated under vacuum, the residue filtered through a pad of silica (eluting with CH2Cl2/PE, 3:7) and the solvent removed under reduced pressure. The residue was purified by recrystallization from CH2Cl2/PE to afford N-{4-chloro-2-[1-(4-chlorophenoxyimino)butyl]phenyl}trifluoromethanesulfonamide 182 (40 mg, 10%), as a yellow solid. M.p. 69-70° C. 1H n.m.r. (200 MHz, CDCl3) δ 7.52, d, J=8.8 Hz, 1H, 7.43, dd, J=2.2 and 8.8 Hz, 1H, 7.25, d, J=9.2 Hz, 2H, 7.18, d, J=2.2 Hz, 1H, 7.01, d, J=9.2 Hz, 2H, 6.43, br s, 1H, 1.33, s, 9H.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationthe residue filtered through a pad of silica (eluting with CH2Cl2/PE, 3:7)
  3. customthe solvent removed under reduced pressure
  4. customThe residue was purified by recrystallization from CH2Cl2/PE

Sources & evidence

ORD record
ord-eae10534eba541398cda1bde085d262d
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

Loading…