Iodine → [(4-Iodo-1h-pyrazole-1-yl)methyl](3,3,3-trifluoropropyl)malononitrile

HRID 1982986Notes

Reaction equation

HRID 1982986 reaction equation
[N:1]1([CH2:6][C:7]([CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])([C:10]#[N:11])[C:8]#[N:9])[CH:5]=[CH:4][CH:3]=[N:2]1.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[I:40]I>C(#N)C>[I:40][C:4]1[CH:3]=[N:2][N:1]([CH2:6][C:7]([CH2:12][CH2:13][C:14]([F:15])([F:16])[F:17])([C:10]#[N:11])[C:8]#[N:9])[CH:5]=1

Participants

5

Reactant 3

HCID 807IodineHCID 9869224Ammonium cerium (IV) nitrateHCID 86612638(1H-pyrazole-1-yl methyl) (3,3,3-trifluoropropyl) malononitrile

Product 1

HCID 87847917[(4-Iodo-1h-pyrazole-1-yl)methyl](3,3,3-trifluoropropyl)malononitrileYield 115.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.21 g of [(1H-pyrazole-1-yl)methyl](3,3,3-trifluoropropyl)malononitrile (the compound of the present invention (1)) was dissolved in 50 ml of acetonitrile. 2.19 g of ammonium cerium (IV) nitrate and 1.02 g of iodine were added to the solution, followed by stirring at room temperature for 10 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.71 g of [(4-iodo-1H-pyrazole-1-yl)methyl] (3,3,3-trifluoropropyl) malononitrile (referred as the compound of the present invention (42), hereinafter) shown by below formula.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cb883457f0b24b578b15600d7e963b5f
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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