Acetic Anhydride → N-(3-ethynylphenyl)acetamide

HRID 1906508Notes

Reaction equation

HRID 1906508 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]#[CH:9])[CH:5]=[CH:6][CH:7]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>>[C:8]([C:4]1[CH:3]=[C:2]([NH:1][C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][CH:5]=1)#[CH:9]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 104682Benzenamine, 3-ethynyl-

Product 1

HCID 2726447N-(3-ethynylphenyl)acetamideYield 89%

Procedure

A 30.0 g (0.256 mole) sample of 3-aminophenylacetylene was cooled at ice bath temperature and 27.0 ml (0.282 mole) of acetic anhydride was added dropwise. The ice bath was removed and the mixture stirred for 30 min. The mixture was diluted with ether and the resulting solution washed with water, NaHCO3 solution and brine. The organic phase was dried (K2CO3) and the solvent evaporated in vacuo. The crystalline residue was recrystallized from CHCl3 -hexane to give 60.7 g (89% yield) of crystalline N-(3-ethynylphenyl)acetamide, mp 94°-96° C.

Workup

  1. additionwas added dropwise
  2. customThe ice bath was removed
  3. additionThe mixture was diluted with ether
  4. washthe resulting solution washed with water, NaHCO3 solution and brine
  5. dry with materialThe organic phase was dried (K2CO3)
  6. customthe solvent evaporated in vacuo
  7. customThe crystalline residue was recrystallized from CHCl3 -hexane

Sources & evidence

ORD record
ord-2fd798472f1f409eac0ca144b019bcba
Source dataset
uspto-grants-1987_03
Patent number
US04652584

Reaction notes

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