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

HRID 47883

Reaktionsgleichung

Reaktionsgleichung von HRID 47883
[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+].[I-].[Na+].[CH3:22][O:23][CH2:24][CH2:25]Br>CC(CC)=O.O>[CH2:1]([C:3]1[N:4]([CH2:25][CH2:24][O:23][CH3:22])[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 5238Sodium IodideHCID 10340Sodium CarbonateHCID 809722-Bromoethyl methyl etherHCID 178438045HCID 178438045, Verbindung

Produkt 1

HCID 112187175-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (25 g, 0.136 Mol), sodium carbonate (18 g, 0.17 Mol) and sodium iodide (20.4 g, 0.136 Mol) were suspended in ethyl methyl ketone (125 mL) at room temperature. 2-bromoethyl methyl ether (12.8 mL, 0.142 Mol) was added and the mixture was heated to reflux and stirred for 70 hours. The mixture was cooled to ambient temperature and water (250 mL) was added. The resultant slurry was warmed to reflux and held at that temperature for 30 min before cooling to room temperature. The resultant precipitate was granulated at room temperature for 3 h, filtered and vacuum dried to afford 5-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide as a yellow crystalline solid 24.3 g, 74%. Data as reported for Example (g)(i).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureThe resultant slurry was warmed
  4. temperatureto reflux
  5. waitheld at that temperature for 30 min
  6. temperaturebefore cooling to room temperature
  7. filtrationfiltered
  8. customvacuum dried

Quellen und Nachweise

ORD-Eintrag
ord-3b5f06b838194b6a9ad7bbc738c90123
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699991B2

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