Acetyl chloride → (E)-N-[2-(6-methoxyindan-1-ylidene)ethyl]acetamide

HRID 582209Notes

Reaction equation

HRID 582209 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8]/[C:9]/2=[CH:12]\[CH2:13][NH2:14])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8]/[C:9]/2=[CH:12]\[CH2:13][NH:14][C:22](=[O:24])[CH3:23])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10987044(E)-1-(2-Aminoethylidene)-6-methoxyindan

Product 1

HCID 59957023(E)-N-[2-(6-methoxyindan-1-ylidene)ethyl]acetamideYield 111.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-2-(6-methoxyindan-1-ylidene)-ethylamine (736 mg, 3.89 mmol) and triethylamine (0.59 g, 5.84 mmol) in tetrahydrofuran (20 ml) was added acetyl chloride (0.37 g, 4.70 mmol) gradually dropwise on an ice bath and the mixture was stirred at room temperature for 2 hours. This reaction mixture was poured in water and extracted with ethyl acetate. The extract was washed serially with saturated saline and water and dried over anhydrous magnesium sulfate. Finally the solvent was distilled off under reduced pressure to provide (E)-N-[2-(6-methoxyindan-1-ylidene)ethyl]acetamide (yield 1.0 g, 90%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed serially with saturated saline and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationFinally the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5e947cf76d3e4318a1128ef636fff228
Source dataset
uspto-grants-1999_07
Patent number
US05922771

Reaction notes

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