Stannous Chloride → N'-[(2'-amino-1,1'-biphenyl-4-yl)methyl]-N'-pentyl-N-(2,4,6-trifluorophenyl)urea

HRID 492291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 492291
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:18](=[O:29])[NH:19][C:20]2[C:25]([F:26])=[CH:24][C:23]([F:27])=[CH:22][C:21]=2[F:28])=[CH:12][CH:11]=1)([O-])=O.[Sn](Cl)Cl>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([CH2:16][N:17]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:18](=[O:29])[NH:19][C:20]2[C:21]([F:28])=[CH:22][C:23]([F:27])=[CH:24][C:25]=2[F:26])=[CH:14][CH:15]=1

Komponenten

4

Edukt 2

HCID 24479Stannous ChlorideHCID 68850802N'-[(2'-nitro-1,1'-biphenyl-4-yl)methyl]-N'-pentyl-N-(2,4,6-trifluorophenyl)urea

Produkt 1

HCID 68850739N'-[(2'-amino-1,1'-biphenyl-4-yl)methyl]-N'-pentyl-N-(2,4,6-trifluorophenyl)ureaAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N′-[(2′-Nitro-1,1′-biphenyl-4-yl)methyl]-N′-pentyl-N-(2,4,6-trifluorophenyl)urea (196.0 mg) and anhydrous tin(II) chloride (401.6 mg) were added to ethanol (4 mL), and the mixture was heated under reflux. One hour later, the solvent was distilled off, and ethyl acetate (15 mL) and a saturated sodium bicarbonate solution (15 mL) were added to the residue. The resultant precipitate was filtered off through Celite. The filtrate was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford N′-[(2′-amino-1,1′-biphenyl-4-yl)methyl]-N′-pentyl-N-(2,4,6-trifluorophenyl)urea (179.2 mg). Yield: 94%.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. distillationOne hour later, the solvent was distilled off
  4. additionethyl acetate (15 mL) and a saturated sodium bicarbonate solution (15 mL) were added to the residue
  5. filtrationThe resultant precipitate was filtered off through Celite
  6. extractionThe filtrate was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-42fdaa6c2b724aecaa3bd4854c7aa27f
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531576B2

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