Nitrogen → 6-(3-Nitro-pyrazol-1-yl)-hexan-2-one

HRID 2064937

Reaktionsgleichung

Reaktionsgleichung von HRID 2064937
N#N.[N+:3]([C:6]1[NH:10][N:9]=[CH:8][CH:7]=1)([O-:5])=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[CH3:23]>C(C#N)(C)=O.CC(=O)OCC.O>[N+:3]([C:6]1[CH:7]=[CH:8][N:9]([CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[CH3:23])[N:10]=1)([O-:5])=[O:4]

Komponenten

8

Edukt 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 250616-Bromohexan-2-oneHCID 1234193-Nitropyrazole

Produkt 1

HCID 620232696-(3-Nitro-pyrazol-1-yl)-hexan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 694302-OxopropiononitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 5-nitro-1H-pyrazole (3.69 g, 29.35 mmol) and Cs2CO3 (10.53 g, 32.28 mmol) in AcCN (34.0 mL) was treated with a solution of 6-bromo-hexan-2-one (5.78 g, 32.28 mmol) in AcCN (26.0 mL). The reaction mixture was stirred at 80° C. for 2 h. Water (123 mL) and EA (185 mL) were added to the cooled reaction mixture. The aq. layer was extracted with EA (185 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (50:50 hept-EA) gave the title compound. TLC: rf (50:50 hept-EA)=0.21. LC-MS-conditions 02: tR=0.82 min; [M+H]+=212.28.

Aufarbeitung

  1. extractionThe aq. layer was extracted with EA (185 mL)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (50:50 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-5f9d0c71e6b440c5b0a05143ae5aa72f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288419B2

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