2,2,2-Trifluoroethanol → 1-[2-(2,2,2-Trifluoroethoxy)-5-pyridylmethyl]-2-(nitroimino)imidazolidine

HRID 22213

Reaktionsgleichung

[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[H][H].[Na].FC(F)(F)CO.Cl[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:30][CH2:29][NH:28][C:27]2=[N:31][N+:32]([O-:34])=[O:33])=[CH:21][N:20]=1>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[F:3][C:4]([F:8])([F:7])[CH2:5][O:6][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:30][CH2:29][NH:28][C:27]2=[N:31][N+:32]([O-:34])=[O:33])=[CH:21][N:20]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Sodium hydride (0.48 g) was added to a solution of 2,2,2-trifluoroethanol (2.4 g) in toluene (30 ml) was added, and the mixture was stirred until the generation of hydrogen ceased. As a result, 2,2,2-trifluoroethanol sodium salt was prepared. To the product were added 1-(2-chloro-5-pyridylmethyl)-2-(nitroimino)imidazolidine (5.1 g) synthesized by the method of Example 3 and a catalytic amount of 4-dimethylaminopyridine. The mixture was heated at 80° C. for 10 hours with stirring. After cooling the reaction mixture, the precipitated crystals were collected by filtration, washed with water and ether and then purified by silica gel chromatography to give 1-[2-(2,2,2-trifluoroethoxy)-5-pyridylmethyl]-2-(nitroimino)imidazolidine (1.5 g).

Aufarbeitung

additionwas added
customsynthesized by the method of Example 3
temperatureAfter cooling the reaction mixture
filtrationthe precipitated crystals were collected by filtration
washwashed with water and ether
custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-37f501ed7b344cf2b37eaf2f0fd15b97
Quelldatensatz: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05428032

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