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

HRID 376990Notes

Reaction equation

[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

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-7c919dc479094f6d97c00db0e47871b7
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06022967

Reaction notes

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