Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)- → 5-Bromo-2-chloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamide

HRID 23823

Reaktionsgleichung

Reaktionsgleichung von HRID 23823
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:15])=[C:6]([CH:14]=1)[C:7]([NH:9][CH2:10][CH:11]=[N:12][OH:13])=[O:8].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.[CH3:37][OH:38].Cl.C([BH3-])#N.[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:15])=[C:6]([CH:14]=1)[C:7]([NH:9][CH2:10][CH2:11][N:12]([CH:37]=[O:38])[OH:13])=[O:8]

Komponenten

6

Edukt 4

HCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5003444Sodium cyanoborohydrideHCID 21893726Hydrochloride methanol2×HCID 739879025-bromo-2-chloro-N-(2-hydroxyimino-ethyl)-benzamide

Produkt 1

HCID 225906105-Bromo-2-chloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamideAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 5-bromo-2-chloro-N-(2-hydroxyimino-ethyl)-benzamide (2 g, 6.9 mmol) in MeOH (75 mL) under an argon atmosphere at 0° C. was added methyl orange (trace) followed by a saturated solution of MeOH/HCl until a persistent red color was observed. Sodium cyanoborohydride (0.52 g, 8.2 mmol) was dissolved in MeOH (10 mL) and was added sequentially with saturated MeOH/HCl over 0.5 h. The reaction mixture was stirred an additional 2 h and the MeOH was removed in vacuo. The residue was basidified with saturated Na2CO3 and extracted (7×25 mL) with dichloromethane/MeOH (9:1). The combined organic extracts were washed with brine, were dried (Na2SO4) and were concentrated to provide the title compound (0.7 g, 35%) as a white solid. ESMS: M+H=293.

Aufarbeitung

  1. customthe MeOH was removed in vacuo
  2. extractionextracted (7×25 mL) with dichloromethane/MeOH (9:1)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialwere dried (Na2SO4)
  5. concentrationwere concentrated

Quellen und Nachweise

ORD-Eintrag
ord-e20624abd66b4a55a6829ef35c4f7191
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852882B2

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