Ammonia → HCID 19760136, Verbindung

HRID 1586934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586934
N.[Na].[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[N:12]=2)[CH:5]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>[N+]([O-])([O-])=O.[Fe+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C(Cl)(Cl)Cl.C(O)C.O>[C:20]1([CH2:19][CH2:3][C:4]2[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([C:11]3[CH:16]=[C:15]([CH2:17][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]=[C:13]([CH3:18])[N:12]=3)[CH:5]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

9

Edukt 4

HCID 222AmmoniaHCID 7498Benzyl BromideHCID 5360545Sodium2×HCID 141486094,4',6,6'-Tetramethyl-2,2'-bipyridine

Produkt 1

HCID 19760136HCID 19760136, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 25251Ferric nitrateKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

To liquid ammonia (20 ml) at -50° C. enough sodium was added to maintain a blue colored solution. Iron (III) nitrate (20 mg) was added and then sodium (0.19 g, 0.008 gr.atom). After 45 minutes 4,4',6,6'-tetramethyl-2,2'-bipyridine (26) (1.06 g, 5.00 mmoles) was added in small portions and the mixture was stirred for 1.5 hours at -50° C. Benzyl bromide (1.88 g, 11.0 mmoles) was added at -50° C. during 2 hours. The mixture was allowed to warm and water (50 ml), ethanol (20 ml) and chloroform (30 ml) was added. The organic phase was extracted with saturated ammonium sulfate solution, dried with magnesium sulfate and evaporated. By addition of ethyl acetate some pure compound was precipitated. The rest was purified by means of flash chromatography (silica, 0-6% methanol/dichloromethane).

Aufarbeitung

  1. temperatureto maintain a blue colored solution
  2. temperatureto warm
  3. extractionThe organic phase was extracted with saturated ammonium sulfate solution
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. additionBy addition of ethyl acetate some pure compound
  7. customwas precipitated
  8. customThe rest was purified by means of flash chromatography (silica, 0-6% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-3c3a9b6599ca4756abac75e7efde9619
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05216134

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