Formic Acid → 2,3,5-Trichloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamide

HRID 23818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 23818
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[Cl:11][C:12]1[C:24]([Cl:25])=[CH:23][C:22]([Cl:26])=[CH:21][C:13]=1[C:14]([NH:16][CH2:17][CH2:18][NH:19][OH:20])=[O:15]>N1C=CC=CC=1>[Cl:11][C:12]1[C:24]([Cl:25])=[CH:23][C:22]([Cl:26])=[CH:21][C:13]=1[C:14]([NH:16][CH2:17][CH2:18][N:19]([CH:8]=[O:10])[OH:20])=[O:15]

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 225906062,3,5-trichloro-N-(2-hydroxyamino-ethyl)-benzamide

Produkt 1

HCID 225905992,3,5-Trichloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamideAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of acetic anhydride (2 mL) and formic acid (1 mL) was allowed to stand at 55° C. for 2.5 h. After cooling to 0° C., the resulting mixed anhydride (0.5 mL) was added to a solution of 2,3,5-trichloro-N-(2-hydroxyamino-ethyl)-benzamide (0.27 g, 1.0 mmol) in pyridine (10 mL) at 0° C. under an argon atmosphere. The reaction mixture was stirred for 2 h at room temperature and the pyridine removed in vacuo. The residue was purified by preparative reverse-phase HPLC to provide the title compound (0.09 g, 28%) as a white solid. 1H NMR* (400 MHz, CD3OD): δ 8.35 (s, 0.5H); 7.95 (s, 0.5H); 7.70 (s, 1H); 7.42 (s, 1H); 3.78 (m, 1H); 3.73 (m, 1H); 3.60 (m, 2H). * 1:1 mixture of rotamers. ESMS: M+H=311.

Aufarbeitung

  1. customthe pyridine removed in vacuo
  2. customThe residue was purified by preparative reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ffa1153d1d2d48b5b2dc75610eabf63f
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852882B2

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