Cesium carbonate → 5-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide

HRID 348412

Reaktionsgleichung

Reaktionsgleichung von HRID 348412
[CH2:1]([C:3]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([C:11]([NH2:13])=[O:12])[NH:5][N:4]=1)[CH3:2].[CH3:14][O:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([C:3]1[N:4]([CH2:17][CH2:16][O:15][CH3:14])[N:5]=[C:6]([C:11]([NH2:13])=[O:12])[C:7]=1[N+:8]([O-:10])=[O:9])[CH3:2]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 178438045HCID 178438045, Verbindung

Produkt 1

HCID 112187175-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (WO, 9849166), (1.7 g, 8.8 mmol), 2-bromoethyl methyl ether (0.85 ml, 8.85 mmol) and cesium carbonate (2.9 g, 9.0 mmol) in N,N-dimethylformamide (20 ml) was stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (125 ml) and brine (100 ml). The phases were separated, and the organic layer was dried (Na2SO4), and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel, using ethyl acetate:methanol (97:3) as eluant to afford the title compound of preparation 1, 831 mg,

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (125 ml) and brine (100 ml)
  3. customThe phases were separated
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel
  7. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-ba2e88d262594634be8af0fd568efffb
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176311B2

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