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

HRID 348424

Reaktionsgleichung

Reaktionsgleichung von HRID 348424
[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].C(=O)([O-])[O-].[Na+].[Na+].[CH3:20][O:21][CH2:22][CH2:23]Br.C(Cl)Cl>C1COCC1.O>[CH2:1]([C:3]1[N:4]([CH2:23][CH2:22][O:21][CH3:20])[N:5]=[C:6]([C:11]([NH2:13])=[O:12])[C:7]=1[N+:8]([O-:10])=[O:9])[CH3:2]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 10340Sodium 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 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (2.5 kg, 13.6 Mol), sodium carbonate (1.8 Kg, 17.0 Mol) and 2-bromoethyl methyl ether (1.98 kg, 14.2 Mol) in THF (22.5 L) and water (2.5 L) was heated under reflux and stirred for 20 hours. The mixture was cooled to ambient temperature and CH2Cl2 (67.5 L) and water (22.5 L) were added. The resultant organic and aqueous layers were separated. The aqueous phase was extracted with CH2Cl2 (22.5 L) and the combined organic solution was distilled under atmospheric pressure and replaced with ethyl acetate (33 L) to a final volume of 17 L. The cooled mixture was granulated at ambient temperature for 2 hours, filtered and washed with ethyl acetate (2.5 L). This afforded 5-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide as a white crystalline solid, 2.10 kg, 57%. m.p.=140° C. Found: C, 44.46; H, 5.79; N, 23.01. C9H14N4O4 requires C, 44.63; H, 5.79; N, 23.14%.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe resultant organic and aqueous layers were separated
  4. extractionThe aqueous phase was extracted with CH2Cl2 (22.5 L)
  5. distillationthe combined organic solution was distilled under atmospheric pressure
  6. waitThe cooled mixture was granulated at ambient temperature for 2 hours
  7. filtrationfiltered
  8. washwashed with ethyl acetate (2.5 L)

Quellen und Nachweise

ORD-Eintrag
ord-9587e5b62c124a949c3ffcecd7c14af6
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176311B2

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