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

HRID 970879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970879
[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])([CH3:19])[CH3:18])[CH:3]=1.Cl.[F:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][NH2:31])=[CH:26][CH:25]=1.CC([O-])=O.[Na+]>CCO>[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](=[N:31][O:30][C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:3]=1

Komponenten

5

Edukt 3

HCID 517045Sodium AcetateHCID 22120336O-(4-fluorophenyl)hydroxylamine hydrochlorideHCID 67270985N-[4-chloro-2-(2,2-dimethylpropionyl)phenyl]trifluoromethanesulfonamide

Produkt 1

HCID 72491712N-{4-chloro-2-[1-(4-fluorophenoxyimino)2,2-dimethylpropyl]phenyl}trifluoromethanesulfonamideAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of N-[4-chloro-2-(2,2-dimethylpropionyl)phenyl]trifluoromethanesulfonamide 29C (280 mg, 0.82 mmol), O-(4-fluorophenyl)hydroxylamine hydrochloride (200 mg, 1.22 mmol) and anhydrous NaOAc (100 mg, 1.22 mmol) in EtOH (20 mL) was stirred for 48 hours at RT. The reaction mixture was concentrated under vacuum and the residue purified by column chromatography (eluting with CH2Cl2/PE, 1:4 to 2:3) to afford N-{4-chloro-2-[1-(4-fluorophenoxyimino)2,2-dimethylpropyl]phenyl}trifluoromethanesulfonamide 198 (40 mg, 11%), as an orange oil. 1H n.m.r. (200 MHz, CDCl3) δ 7.52, d, J=8.8 Hz, 1H; 7.42, dd, J=2.2 and 8.8 Hz, 1H; 7.19, d, J=2.2 Hz, 1H; 7.00, m, 4H; 6.49, br s, 1H; 1.32, s, 9H. HRMS (M+) 452.0576.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue purified by column chromatography (eluting with CH2Cl2/PE, 1:4 to 2:3)

Quellen und Nachweise

ORD-Eintrag
ord-4b46b7d0007d4f978d5ff988c537efab
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312248B2

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