Iodine → HCID 68706611, compound

HRID 2067938Notes

Reaction equation

HRID 2067938 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:8]([CH3:18])[N:7]=1)=[O:5])[CH3:2].[I:19]I.[N+]([O-])([O-])=O.[NH4+].[Ce]>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([I:19])=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:8]([CH3:18])[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 807IodineHCID 57418452Ammonium cerium-nitrateHCID 68709923HCID 68709923, compound

Product 1

HCID 68706611HCID 68706611, compoundYield 161.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a well stirred solution of 2.79 g of 5-(4-Fluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid ethyl ester in 100 ml of Acetonitrile were added 1.71 g of Iodine and 3.70 g of Cerium ammonium nitrate. The mixture was stirred for 3 h at 50° C. The red solution was then allowed to cool and was concentrated in vaccuo. The residue was taken up in 200 ml of Ethyl acetate. The organic phase was successively washed with 5% Sodium bisulfite solution and brine. After drying over Magnesium sulfate and concentration, a beige solid 4.06 g (96%) was obtained which is sufficiently pure and was directly used in the next step. MS: m/e=375.3 ([M+1]+).

Workup

  1. temperatureto cool
  2. concentrationwas concentrated in vaccuo
  3. washThe organic phase was successively washed with 5% Sodium bisulfite solution and brine
  4. dry with materialAfter drying over Magnesium sulfate and concentration

Sources & evidence

ORD record
ord-e5ffa86961344987a6fcd4b75e9d78e2
Source dataset
uspto-grants-2012_10
Patent number
US08293916B2

Reaction notes

Loading…