Stannous chloride dihydrate → (4-aminophenyl)(1-methyl-1H-imidazol-5-yl)methanone

HRID 926467

Reaktionsgleichung

Reaktionsgleichung von HRID 926467
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)=[O:8])=[CH:5][N:4]=[CH:3]1.O.O.[Sn](Cl)Cl>CCO>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]([C:6]2[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=2)=[O:8])=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 86715600(1-Methyl-1H-imidazol-5-yl)(4-nitrophenyl)methanone

Produkt 1

HCID 90101950(4-aminophenyl)(1-methyl-1H-imidazol-5-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of (1-methyl-1H-imidazol-5-yl)(4-nitrophenyl)methanone (1.30 g, 5.62 mmol, Intermediate 15: step b and tin(II)chloride dihydrate (6.54 g, 28.1 mmol) in EtOH (35 mL) was stirred at reflux for 1 hour, cooled to room temperature and evaporated in vacuo to remove most of the EtOH. The residue was poured into a 3 M aqueous NaOH/ice solution rinsing with EtOAc. The mixture was stirred at room temperature for 15 minutes then layers were separated. The aqueous layer was again extracted with EtOAc. The combined EtOAc extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to provide the title compound as a yellow solid.

Aufarbeitung

  1. temperatureat reflux for 1 hour
  2. customevaporated in vacuo
  3. customto remove most of the EtOH
  4. additionThe residue was poured into a 3 M aqueous NaOH/ice solution
  5. washrinsing with EtOAc
  6. customlayers were separated
  7. extractionThe aqueous layer was again extracted with EtOAc
  8. washThe combined EtOAc extracts were washed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3cfb7b3b13dd4f09b07c33441e71498c
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284308B2

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