N-(3-ethynylphenyl)acetamide → Acetamide, N,N′-(1-buten-3-yne-1,4-diyldi-3,1-phenylene)bis-

HRID 971981Notes

Reaction equation

HRID 971981 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]#[CH:12])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]>C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:12]#[C:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 2726447N-(3-ethynylphenyl)acetamide

Product 1

HCID 54032150Acetamide, N,N′-(1-buten-3-yne-1,4-diyldi-3,1-phenylene)bis-Yield 96.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 350 ml of deoxygenated acetic acid was added 1.4 g of cuprous acetate whereupon a clear blue solution formed. The solution was brought to reflux, under nitrogen, and 14.35 g (0.09 mole) of 3-acetamidophenylacetylene was added as a solid. The reaction mixture was maintained at reflux for 12 hours and cooled to room temperature. Isolation of the material was carried out by precipitation of the reaction mixture into distilled water and collection by filtration. The light tan material was air dried and recrystallized from isopropanol to give 13.8 g of product (96% yield) (m.p. 276°-278° C.).

Workup

  1. customformed
  2. temperatureto reflux, under nitrogen
  3. temperatureThe reaction mixture was maintained
  4. temperatureat reflux for 12 hours
  5. customIsolation of the material was carried out by precipitation of the reaction mixture
  6. distillationinto distilled
  7. customwater and collection
  8. filtrationby filtration
  9. customdried
  10. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-f38b939bd26b4622ada2c7df436fc9c7
Source dataset
uspto-grants-1979_07
Patent number
US04162265

Reaction notes

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