HCID 59333282, Verbindung → HCID 59333338, Verbindung

HRID 1893488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1893488
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[C:12]([N+:20]([O-])=O)=[CH:11][C:10]=1[C:23]([F:26])([F:25])[F:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[C:12]([NH2:20])=[CH:11][C:10]=1[C:23]([F:26])([F:24])[F:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 59333282HCID 59333282, VerbindungHCID 85782573Tin tetrachloride dihydrate

Produkt 1

HCID 59333338HCID 59333338, VerbindungAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of N-benzyl-5-(1H-imidazol-1-yl)-4-nitro-2-(trifluoromethyl)aniline (190 mg; 0.52 mmol; 1 eq) and tin chloride dihydrate (591 mg; 2.62 mmol; 5 eq) in ethanol (2 ml) is stirred under argon at 80° C. for 4 h. Concentration, partition (ethyl acetate/aqueous sodium hydrogenocarbonate), addition of solid sodium hydrogenocarbonate to adjust the pH around 8, filtration over Celite, extraction of the cake solid with ethyl acetate, reunion of the organic phases, additional washings (aqueous ammonium chloride, brine), drying (magnesium sulfate) and concentration affords the title product (165 mg; 0.50 mmol; 96%) as a yellow solid.

Aufarbeitung

  1. concentrationConcentration
  2. custompartition
  3. addition(ethyl acetate/aqueous sodium hydrogenocarbonate), addition of solid sodium hydrogenocarbonate
  4. filtrationthe pH around 8, filtration
  5. extractionover Celite, extraction of the cake solid with ethyl acetate, reunion of the organic phases, additional washings (aqueous ammonium chloride, brine)
  6. customdrying
  7. concentration(magnesium sulfate) and concentration

Quellen und Nachweise

ORD-Eintrag
ord-c2001724a2614fefa0682d2a474a7731
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513250B2

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