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

HRID 379290Notes

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-c5a9aa99654b411d826872bdb1524811
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06297374B1

Reaction notes

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