Acetic Anhydride → N-(3-ethynylphenyl)acetamide

HRID 971980Notes

Reaction equation

HRID 971980 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:10]=[C:11]([C:15]#[CH:16])[CH:12]=[CH:13][CH:14]=1>C(O)(=O)C>[C:5]([NH:8][C:9]1[CH:10]=[C:11]([C:15]#[CH:16])[CH:12]=[CH:13][CH:14]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 104682Benzenamine, 3-ethynyl-

Product 1

HCID 2726447N-(3-ethynylphenyl)acetamideYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 250 ml 3-neck flask fitted with a condenser, nitrogen inlet and outlet, and magnetic stirrer was added 150 ml of acetic acid and 35 ml of acetic anhydride. The mixture was heated to reflux under nitrogen and cooled under nitrogen. To the cooled mixture was added 15 g (0.114 mole) of 3-aminophenylacetylene and the homogeneous solution was refluxed overnight. The cooled reaction mixture was transferred to a 500 ml one-neck flask, and the acetic acid was removed by a rotor-evaporator under high vacuum. Water (200 ml) was added to the residual oil to crystallize the solid product. The material was isolated by filtration and washed with water and then air dried. Recrystallization from carbon tetrachloride with 200 g/10 g solid plus charcoal yielded 14.4 g (79% yield) of a white crystalline product (m.p. 94°-96° C.).

Workup

  1. customTo a 250 ml 3-neck flask fitted with a condenser, nitrogen inlet and outlet, and magnetic stirrer
  2. temperatureThe mixture was heated
  3. temperatureto reflux under nitrogen
  4. temperaturecooled under nitrogen
  5. temperaturethe homogeneous solution was refluxed overnight
  6. customThe cooled reaction mixture
  7. customwas transferred to a 500 ml one-neck flask
  8. customthe acetic acid was removed by a rotor-evaporator under high vacuum
  9. additionWater (200 ml) was added to the residual oil
  10. customto crystallize the solid product
  11. customThe material was isolated by filtration
  12. washwashed with water
  13. customair dried
  14. customRecrystallization from carbon tetrachloride with 200 g/10 g solid plus charcoal

Sources & evidence

ORD record
ord-9ef63c0867b84773bb4d977887e8b9f7
Source dataset
uspto-grants-1979_07
Patent number
US04162265

Reaction notes

Loading…