Sodium Iodide → HCID 28586072, compound

HRID 1096249Notes

Reaction equation

HRID 1096249 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].Br[CH2:14][C:15]#[N:16].[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC#N>[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:5]=[C:6]([NH:7][CH2:14][C:15]#[N:16])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 11534BromoacetonitrileHCID 737533-(Trifluoromethoxy)aniline

Product 1

HCID 28586072HCID 28586072, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(trifluoromethoxy)aniline (1.00 g, 5.64 mmol), bromoacetonitrile (745 mg, 6.21 mmol), sodium iodide (1.86 g, 12.4 mmol), and sodium carbonate (858 mg, 6.21 mmol) in CH3CN (15 mL) was heated at reflux for 18 h, then partitioned between water and EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc gradient) afforded the title compound (904 mg, 74%). Brown liquid, MS: 215.2 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. custompartitioned between water and EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a6c67643e06d4bbe91df31621b5487b7
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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