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Dimethylformamide → 1-(3-Methoxy-2-nitro-6-methylpyridylmethyl)-2-nitromethyleneimidazolidine

HRID 622704
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 622704
[N+:1]([CH:4]=[C:5]1[NH:9][CH2:8][CH2:7][NH:6]1)([O-:3])=[O:2].[H-].[Na+].[H][H].[CH3:14][O:15][C:16]1[C:17]([N+:24]([O-:26])=[O:25])=[N:18][C:19]([CH2:22]Br)=[CH:20][CH:21]=1.[CH3:27]N(C)C=O>>[CH3:14][O:15][C:16]1[C:17]([N+:24]([O-:26])=[O:25])=[N:18][C:19]([CH3:22])=[CH:20][C:21]=1[CH2:27][N:6]1[CH2:7][CH2:8][NH:9][C:5]1=[CH:4][N+:1]([O-:3])=[O:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 30147632-(Nitromethylene)imidazolidineHCID 144051243-Methoxy-2-nitro-6-pyridylmethyl bromideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86742440
1-(3-Methoxy-2-nitro-6-methylpyridylmethyl)-2-nitromethyleneimidazolidine

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Nitromethyleneimidazolidine (1.3 g) was dissolved in dry dimethylformamide (15 ml), and sodium hydride (0.26 g) was added. The mixture was stirred at room temperature until the generation of hydrogen ceased. Subsequently, a solution of 2.4 g of 3-methoxy-2-nitro-6-pyridylmethyl bromide in 5 ml of dimethylformamide was added, and the mixture was stirred at 60° C. for 15 minutes. The reaction mixture was cooled to room temperature, poured into 50 ml of ice water, and extracted with dichloromethane. Dichloromethane was distilled off under reduced pressure, and ethanol was added to the residue to precipitate crystals. The crystals were collected by filtration and washed with ethanol to give 1-(3-methoxy-2-nitro-6-methylpyridylmethyl)-2-nitromethyleneimidazolidine (0.4 g). mp. 177°-181° C.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with dichloromethane
  3. distillationDichloromethane was distilled off under reduced pressure, and ethanol
  4. additionwas added to the residue
  5. customto precipitate crystals
  6. filtrationThe crystals were collected by filtration
  7. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4cdc866464844c1c9043c9b082818713
Quelldatensatz
uspto-grants-1988_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04772620

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