2,3-Dichloropyrazine → HCID 90303493, Verbindung

HRID 62453

Reaktionsgleichung

Reaktionsgleichung von HRID 62453
C(/[N:14]=[CH:15]/[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:36][C:37]1[C:42](Cl)=[N:41][CH:40]=[CH:39][N:38]=1>C1COCC1>[NH2:14][CH:15]([C:42]1[C:37]([Cl:36])=[N:38][CH:39]=[CH:40][N:41]=1)[C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 785752,3-DichloropyrazineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 178497919HCID 178497919, Verbindung

Produkt 1

HCID 90303493HCID 90303493, VerbindungAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of (E)-methyl 4-((benzhydrylimino)methyl)benzoate (67 g, 204 mmol) in THF (700 mL) was cooled to 0° C. and added dropwise NaHMDS (244 mL, 244 mmol). The mixture was stirred at this temperature for 30 minutes, and added a solution of 2,3-dichloropyrazine (33.2 g, 224 mmol) in THF (40 mL). The reaction mixture was stirred at 0° C. for 20 minutes and RT for 40 minutes. After the reaction was completed, the reaction mixture was extracted with EA and water. The organic layer was treated with 3M HCl (500 mL) for 10 minutes. The phases were separated and the organic layer was extracted with 3M HCl. The aqueous was washed with EA and then alkalified with Na2CO3 to pH=9. The aqueous solution was extracted with EA and the combined organics were dried and concentrated to give methyl 4-(amino(3-chloropyrazin-2-yl)methyl)benzoate (46 g, yield 81%).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 0° C. for 20 minutes and RT for 40 minutes
  2. extractionthe reaction mixture was extracted with EA and water
  3. additionThe organic layer was treated with 3M HCl (500 mL) for 10 minutes
  4. customThe phases were separated
  5. extractionthe organic layer was extracted with 3M HCl
  6. washThe aqueous was washed with EA
  7. extractionThe aqueous solution was extracted with EA
  8. customthe combined organics were dried
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f78ef12cdd7844ecb1edb41d70388ec3
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446130B2

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