1-(4-Fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-5-carboxamide → 1-(4-Fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-5-carbonitrile

HRID 432045Notes

Reaction equation

HRID 432045 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([NH2:19])=O)=[CH:14][CH:15]=3)[C:10](=[O:20])[O:9]2)=[CH:4][CH:3]=1>S(Cl)(Cl)=O.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]#[N:19])=[CH:14][CH:15]=3)[C:10](=[O:20])[O:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 467816181-(4-Fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-5-carboxamide

Product 1

HCID 187618171-(4-Fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 1-(4-fluoro-phenyl)-3-oxo-1,3-dihydro-isobenzofuran-5-carboxylic acid amide (13.6 g, 0.05 mole) in thionyl chloride (40 mL) and DMF (0.25 mL) was heated at reflux for 2 hours. The thionyl chloride was then evaporated, and the residue was dissolved in hot IPA (100 mL). On cooling, crystals of the title compound were formed. Yield: 7.8 g (62%). 1H NMR (d6-DMSO): δ 6.87 (s, 1H), 7.26 (t, 2H), 7.42 (dd, 2H), 7.58 (d, 1H), 8.18 (dd, 1H), 8.48 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe thionyl chloride was then evaporated
  4. dissolutionthe residue was dissolved in hot IPA (100 mL)
  5. temperatureOn cooling

Sources & evidence

ORD record
ord-ba1780a7565249908ba0eea4a77dd709
Source dataset
uspto-grants-2003_12
Patent number
US06660873B2

Reaction notes

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