Trifluoroacetic acid → HCID 19419293, compound

HRID 374522Notes

Reaction equation

HRID 374522 reaction equation
[CH:1]([CH2:3][NH:4][C:5]([C:9]1[O:10][CH:11]=[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=12)=[CH:6][C:7]#[N:8])=O.FC(F)(F)C(O)=O>O>[O:10]1[C:11]2[CH:12]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:13]=[C:9]1[C:5]1[NH:4][CH:3]=[CH:1][C:6]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86749185HCID 86749185, compound

Product 1

HCID 19419293HCID 19419293, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

β-[(Formylmethyl)amino]-2-benzofuranacrylonitrile (1.00 g, 3.33 mmol) is added dropwise to trifluoroacetic acid (5 mL). The reaction mixture is stirred at room temperature for one hour, diluted with water and extracted with ethyl acetate. The organic extract is washed sequentially with saturated sodium hydrogen carbonate solution and brine, dried over MgSO4, decolorized with charcoal and concentrated in vacuo to obtain an orange solid. Dry column chromatography of the solid using silica gel and methylene chloride gives the title product as a brown-white solid (0.32 g 46% mp 157°-160.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washis washed sequentially with saturated sodium hydrogen carbonate solution and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto obtain an orange solid
  7. customDry column chromatography of the solid

Sources & evidence

ORD record
ord-300e27b72f9f454b8b8e4098d4c2d88f
Source dataset
uspto-grants-1996_01
Patent number
US05480902

Reaction notes

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