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

HRID 602617Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602617
[C:1]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[NH:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])(=O)[CH2:2][CH2:3][CH3:4].Cl.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][NH2:30])=[CH:25][CH:24]=1.CC([O-])=O.[Na+]>CCO>[Cl:12][C:10]1[CH:9]=[CH:8][C:7]([NH:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])=[C:6]([C:1](=[N:30][O:29][C:26]2[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=2)[CH2:2][CH2:3][CH3:4])[CH:11]=1

Komponenten

5

Edukt 3

HCID 517045Sodium AcetateHCID 20445467O-(4-chlorophenyl)hydroxylamine hydrochlorideHCID 67270216N-(2-butyryl-4-chlorophenyl)trifluoromethanesulfonamide

Produkt 1

HCID 73021830N-{4-chloro-2-[1-(4-chlorophenoxyimino)butyl]phenyl}trifluoromethanesulfonamideAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of N-(2-butyryl-4-chlorophenyl)trifluoromethanesulfonamide 29A (333 mg, 1.0 mmol), O-(4-chlorophenyl)hydroxylamine hydrochloride (200 mg, 1.10 mmol) and anhydrous NaOAc (91 mg, 1.10 mmol) in EtOH (30 mL) was stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum, the residue filtered through a pad of silica (eluting with CH2Cl2/PE, 1:4) and the solvent removed under reduced pressure. The residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:19 to 3:7) to afford N-{4-chloro-2-[1-(4-chlorophenoxyimino)butyl]phenyl}trifluoromethanesulfonamide 166 (283 mg, 62%), as a yellow solid. M.p. 62.5-64.5° C. 1H n.m.r. (200 MHz, CDCl3) δ 11.27, br s, 1H, 7.72, d, J=8.8 Hz, 1H; 7.57d, J=2.4 Hz, 1H, 7.41, dd, J=2.4 and 8.8 Hz, 1H; 7.35, d, J=8.8 Hz, 2H, 7.11, d, J=8.8 Hz, 2H; 2.98, m, 2H, 1.71, sextet, 2H, 1.09, t, J=7.4 Hz,

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationthe residue filtered through a pad of silica (eluting with CH2Cl2/PE, 1:4)
  3. customthe solvent removed under reduced pressure
  4. customThe residue was purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:19 to 3:7)

Quellen und Nachweise

ORD-Eintrag
ord-875e67a5a25e445bb434e55ee4bfdb03
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906538B2

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