Sodium Acetate → 3-((5-Chloro-3-fluoro-pyridin-2-yl)-hydrazono)-1,1,1-trifluoropropan-2-one

HRID 840532Notes

Reaction equation

Br[CH:2](Br)[C:3]([C:5]([F:8])([F:7])[F:6])=[O:4].C([O-])(=O)C.[Na+].[NH:15]([C:17]1[C:22]([F:23])=[CH:21][C:20]([Cl:24])=[CH:19][N:18]=1)[NH2:16]>O>[Cl:24][C:20]1[CH:21]=[C:22]([F:23])[C:17]([NH:15][N:16]=[CH:2][C:3](=[O:4])[C:5]([F:8])([F:7])[F:6])=[N:18][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6.75 g 1,1-dibromo-3,3,3-trifluoroacetone were stirred for 30 min. at 80° C. in a solution of 9.0 g sodium acetate in 250 ml water. Then the solution was cooled at 0° C. and 4.0 g 2-hydrazino-3-fluoro-5-chloropyridin were added. Stirring was continued for 3.5 hrs. Then the reaction mixture was extracted with ethyl acetate, the extracts were washed with water and dried. After evaporation, the remaining residue was purified on silcagel (hexane-ethyl acetate 8:2) to give the title compound as brownish residue which was directly used for the next step. MS: (M−H )=268.

Workup

extractionThen the reaction mixture was extracted with ethyl acetate
washthe extracts were washed with water
customdried
customAfter evaporation
customthe remaining residue was purified on silcagel (hexane-ethyl acetate 8:2)

Sources & evidence

ORD record: ord-5724263dcfb546e1b4a88b0ff77253f2
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369002B1

Reaction notes

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