3-(2-(2,5-Difluorophenyl)hydrazinyl)propanenitrile → HCID 178511141, compound

HRID 1466577Notes

Reaction equation

HRID 1466577 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][NH:10][CH2:11][CH2:12][C:13]#[N:14]>S(=O)(=O)(O)O.O.S([O-])([O-])(=O)=O.[Fe+3].S([O-])([O-])(=O)=O.S([O-])([O-])(=O)=O.[Fe+3].S([O-])([O-])(=O)=O.[Fe+2]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1/[N:9]=[N:10]/[CH2:11][CH2:12][C:13]#[N:14]

Participants

5

Reactant 1

HCID 668471273-(2-(2,5-Difluorophenyl)hydrazinyl)propanenitrile

Product 1

HCID 178511141HCID 178511141, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 24393Ferrous SulfateCatalystHCID 167265Ferric sulfate hydrateCatalystHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 3-(2-(2,5-difluorophenyl)hydrazinyl)propanenitrile (790 mg) in 15 mL of 2N sulfuric acid was added 2.0 g of iron(III) sulfate hydrate. The reaction mixture was stirred at ambient temperature for 30 min as the iron sulfate slowly dissolved and a yellow oil precipitated. The reaction mixture was extracted with ether, and the extracts were washed with water, brine, dried over sodium sulfate, filtered through a plug of silica gel and concentrated to give 710 mg (91%) of (E)-3-((2,5-difluorophenyl)diazenyl)propanenitrile. LCMS (ESI) m+H=196.2. 1H NMR (400 MHz, CDCl3) δ 7.34-7.08 (m, 3H), 4.54-4.31 (m, 2H), 2.99 (t, 2H).

Workup

  1. dissolutionslowly dissolved
  2. customa yellow oil precipitated
  3. extractionThe reaction mixture was extracted with ether
  4. washthe extracts were washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered through a plug of silica gel
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fda8bb9e28b04d598f8243909c36dcef
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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