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Water → 1-(2-Chloro-5-pyridylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine

HRID 862390
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 862390
[CH3:1][N:2]1[CH2:7][NH:6][C:5](=[N:8][N+:9]([O-:11])=[O:10])[NH:4][CH2:3]1.[H-].[Na+].[Cl:14][C:15]1N=[CH:19][C:18]([CH2:21]Cl)=[CH:17][N:16]=1.O.[CH3:24]N(C)C=O.CN(C=O)C>CN(C=O)C>[Cl:14][C:15]1[CH:24]=[CH:19][C:18]([CH2:21][N:6]2[CH2:7][N:2]([CH3:1])[CH2:3][NH:4][C:5]2=[N:8][N+:9]([O-:11])=[O:10])=[CH:17][N:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 962WaterHCID 24758Sodium hydrideHCID 17824068DMF dimethylformamideHCID 220528832-Chloro-5-(chloromethyl)pyrimidineHCID 1354673605-Methyl-2-nitroimino-hexahydro-1,3,5-triazine

Produkt 1

HCID 1364010691-(2-Chloro-5-pyridylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Methyl-2-nitroimino-hexahydro-1,3,5-triazine (3.0 g) was dissolved in dimethylformamide/DMF (20 ml), followed by portionwise addition of sodium hydride (950 mg: oil free) thereto at a temperature in the range of from 0° to 5° C. After one hour stirring at 0° to 5° C. a solution of 2-chloro-5-chloromethyl-pyrimidine (3.1 g) in 20 ml of DMF was added dropwise to the solution, the temperature was kept constant, followed by a five hour stirring. The reaction mixture thus obtained was poured into iced water, subjected to extraction with methylene chloride a few times and then the extract was dried with anhydrous magnesium sulfate which was removed from the solvent. The thus obtained residue was purified by silica gel column chromatography (eluant: ethanol: chloroform=1: 20), to obtain the desired 1-(2-chloro-5-pyridylmethyl)-5-methyl-2-nitroimino-hexahydro-1,3,5-triazine (3.7 g) having a melting point in the range of from 160° to 161° C.

Aufarbeitung

  1. customof from 0° to 5° C
  2. additionwas added dropwise to the solution
  3. customThe reaction mixture thus obtained
  4. extractionsubjected to extraction with methylene chloride a few times
  5. dry with materialthe extract was dried with anhydrous magnesium sulfate which
  6. customwas removed from the solvent
  7. customThe thus obtained residue was purified by silica gel column chromatography (eluant: ethanol: chloroform=1: 20)

Quellen und Nachweise

ORD-Eintrag
ord-4226ff06c93043f4bde3603d05b18598
Quelldatensatz
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05719146

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