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

HRID 432044Notes

Reaction equation

HRID 432044 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](O)=[O:18])=[CH:14][CH:15]=3)[C:10](=[O:20])[O:9]2)=[CH:4][CH:3]=1.[NH3:21]>S(Cl)(Cl)=O.C1(C)C=CC=CC=1>[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]([NH2:21])=[O:18])=[CH:14][CH:15]=3)[C:10](=[O:20])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 99433991-(4-Fluorophenyl)-1,3-dihydro-3-oxo-5-isobenzofurancarboxylic acid

Product 1

HCID 467816181-(4-Fluorophenyl)-3-oxo-1,3-dihydro-2-benzofuran-5-carboxamideYield 80%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A stirred suspension of 1-(4-fluoro-phenyl)-3-oxo-1,3-dihydro-isobenzofuran-5-carboxylic acid (1 g, 3.7 mmol) in thionyl chloride (25 mL) was heated at reflux for 25 min, during which time the solid dissolved. The thionyl chloride was then evaporated, and the residue was dissolved in toluene, and again evaporated. The residue was dissolved in toluene (15 mL) and was treated with a solution of ammonia in ether and a heavy precipitate formed. The mixture was stirred overnight, diluted with toluene and aqueous ammonia solution, and filtered. The residue was dried to give the title compound as a white solid (0.80 g, 80%). 1H NMR (d6-DMSO): δ 6.81 (s, 1H), 7.25 (t, 2H), 7.40 (dd, 2H), 7.54 (d, 1H), 7.59 (bs, 1H), 8.24 (bs, 1H), 8.24 (dd, 1H), 8.42 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 25 min, during which time the solid
  3. dissolutiondissolved
  4. customThe thionyl chloride was then evaporated
  5. dissolutionthe residue was dissolved in toluene
  6. customagain evaporated
  7. dissolutionThe residue was dissolved in toluene (15 mL)
  8. additionwas treated with a solution of ammonia in ether
  9. customa heavy precipitate formed
  10. filtrationfiltered
  11. customThe residue was dried

Sources & evidence

ORD record
ord-6906c31edb3e4dc8810e57e767090f6e
Source dataset
uspto-grants-2003_12
Patent number
US06660873B2

Reaction notes

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