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

HRID 602596Notes

Reaction equation

HRID 602596 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])(=O)[CH3:2].Cl.[F:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][NH2:28])=[CH:23][CH:22]=1.CC([O-])=O.[Na+]>CCO>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([NH:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])=[C:4]([C:1](=[N:28][O:27][C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)[CH3:2])[CH:9]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 22120336O-(4-fluorophenyl)hydroxylamine hydrochlorideHCID 67271047N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide

Product 1

HCID 86603997N-{4-chloro-2-[1-(4-fluorophenoxyimino)ethyl]phenyl}trifluoromethanesulfonamideYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide 19 (350 mg, 1.16 mmol), O-(4-fluorophenyl)hydroxylamine hydrochloride (190 mg, 1.16 mmol) and anhydrous NaOAc (104 mg, 1.27 mmol) in EtOH (16 mL) was stirred for 15 h at RT. The reaction mixture was concentrated under vacuum, the residue filtered through a pad of silica (eluting with CH2Cl2/PE, 3:2) and the solvent removed under reduced pressure. The residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:4) to afford N-{4-chloro-2-[1-(4-fluorophenoxyimino)ethyl]phenyl}trifluoromethanesulfonamide 129 (458 mg, 96%), as a pale yellow solid. M.p. 71-73° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.23, br s, 1H, 7.69, d, J=9.0 Hz, 1H; 7.59, d, J=2.4 Hz, 1H, 7.40, dd, J=2.4 and 9.0 Hz, 1H, 7.18-7.03, m, 4H, 2.55, s, 3H.

Workup

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

Sources & evidence

ORD record
ord-8734c6ba8656437480f085c87ca4aacd
Source dataset
uspto-grants-2011_03
Patent number
US07906538B2

Reaction notes

Loading…