Acetic Acid → 3-oxo-1-phenyl-1,3-dihydro-2-benzofuran-1-carboxamide

HRID 1279223Notes

Reaction equation

HRID 1279223 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#[N:19].[K+].[C:21]([OH:24])(=O)C>>[O:13]=[C:11]1[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:21]([NH2:19])=[O:24])[O:12]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 68132-Benzoylbenzoic AcidHCID 9032Potassium Cyanide

Product 1

HCID 2334123-oxo-1-phenyl-1,3-dihydro-2-benzofuran-1-carboxamide

Conditions

Temperature
120 °C

Procedure

A mixture of 2-benzoylbenzoic acid (75 g), potassium cyanide (35 g), and glacial acetic acid (175 mL) was heated at 115-125° C. in a sealed pressure bottle for 70 h. After cooling to ambient temperature, the precipitated solid was collected by filtration, washed with water and ethanol then crystallized from ethanol to give the title compound (45 g), m. p. 225-227° C.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water and ethanol
  4. customthen crystallized from ethanol

Sources & evidence

ORD record
ord-770a571a64ed43dcb1fc1e8e97657176
Source dataset
uspto-grants-2002_09
Patent number
US06448255B1

Reaction notes

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