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N-Methoxy-N-methyl-5-nitro-3-pentafluorosulfanylbenzamide → 3-Amino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamide

HRID 532412
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 532412
[CH3:1][O:2][N:3]([CH3:21])[C:4](=[O:20])[C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[C:7]([S:14]([F:19])([F:18])([F:17])([F:16])[F:15])[CH:6]=1.[H][H]>CO.[Ni]>[NH2:11][C:9]1[CH:10]=[C:5]([CH:6]=[C:7]([S:14]([F:19])([F:15])([F:16])([F:17])[F:18])[CH:8]=1)[C:4]([N:3]([O:2][CH3:1])[CH3:21])=[O:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 58136777N-Methoxy-N-methyl-5-nitro-3-pentafluorosulfanylbenzamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 580857033-Amino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamideAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

N-Methoxy-N-methyl-5-nitro-3-pentafluorosulfanylbenzamide (4.2 g) was dissolved in methanol (120 ml), and Raney nickel (approx. 700 mg) was added. With a hydrogen balloon attached, hydrogenation was effected on a magnetic stirrer. After 5 h, the catalyst was filtered off and washed with methanol. The filtrate was concentrated under reduced pressure and the residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed of the acetonitrile, basified with sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 1.73 g of the desired compound were obtained.

Aufarbeitung

  1. customhydrogenation was effected on a magnetic stirrer
  2. filtrationthe catalyst was filtered off
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by means of preparative HPLC
  6. extractionextracted three times with ethyl acetate
  7. dry with materialThe combined extracts were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b122898c38b14d4990be011b97667f7d
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08853206B2

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