Acetyl chloride → HCID 22004791, compound

HRID 1636610Notes

Reaction equation

HRID 1636610 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].Cl.[CH2:6]1[CH2:10][O:9][C:8]2[CH:11]=[CH:12][C:13]3[CH2:14][CH:15]=[C:16]([CH2:18][CH2:19][NH2:20])[C:17]=3[C:7]1=2.C(N(CC)CC)C>CN(C)C=O>[CH2:6]1[CH2:10][O:9][C:8]2[CH:11]=[CH:12][C:13]3[CH2:14][CH:15]=[C:16]([CH2:18][CH2:19][NH:20][C:1](=[O:3])[CH3:2])[C:17]=3[C:7]1=2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22004822HCID 22004822, compound

Product 1

HCID 22004791HCID 22004791, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acetyl chloride (0.24 g, 3.03 mmol) was slowly added dropwise to an ice-cooled solution of 2-(1,6-dihydro-2H-indeno[5,4-b]furan-8-yl)ethylamine hydro-chloride (0.6 g, 2.52 mmol) and triethylamine (0.64 g, 6.31 mmol) in N,N-dimethylformamide (60 mL). After overnight stirring at room temperature, the reaction mixture was concentrated and poured into water, and the organic matter was extracted with ethyl acetate. The extract was washed with a satruated aqueous sodium chloride solution and water and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was purified by silica gel column chromatography (ethyl acetate:methanol=98:2) and further recrystallized from ethyl acetate to give 425 mg (yield: 70%) of the target compound.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionpoured into water
  3. extractionthe organic matter was extracted with ethyl acetate
  4. washThe extract was washed with a satruated aqueous sodium chloride solution and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography (ethyl acetate:methanol=98:2)
  9. customfurther recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-de891719ccb34573a513bbd71bdd14f7
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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