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

HRID 602619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602619
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 73021830N-{4-chloro-2-[1-(4-chlorophenoxyimino)butyl]phenyl}trifluoromethanesulfonamideAusbeute 10,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-eae10534eba541398cda1bde085d262d
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906538B2

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