Acetyl chloride → N-(6-acetyl-2,3-dihydro-1H-inden-5-yl)acetamide

HRID 1654541Notes

Reaction equation

HRID 1654541 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11](=[O:13])[CH3:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:14](Cl)(=[O:16])[CH3:15].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[C:14]([C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][CH2:2][CH2:1]2)=[CH:5][C:6]=1[NH:10][C:11](=[O:13])[CH3:12])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 583823N-(2,3-Dihydro-1H-inden-5-yl)acetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18997251N-(6-acetyl-2,3-dihydro-1H-inden-5-yl)acetamideYield 48.3%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a stirred mixture of 10.5 g of N-(2,3-dihydro- 1H-inden-5-yl)acetamide and 4.7 ml of acetyl chloride in 100 ml of carbondisulfide were added portionwise 17.3 g of aluminum chloride at room temperature. After stirring for 2 hours at reflux temperature, the cooled reaction mixture was poured into 50 ml ice/HCl. The separated aqueous layer was extracted with dichloromethane. The extract was combined with the former organic layer, washed with water, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; dichloromethane/methanol 99:1 ). The eluent of the desired fraction was evaporated and the residue was crystallized from 2,2'-oxybispropane. The crystallized product was filtered off and dried, yielding 6.3 g (48.3%) of N-(6-acetyl-2,3-dihydro-1H-inden-5-yl)acetamide (interm. 1).

Workup

  1. temperatureat reflux temperature
  2. customthe cooled reaction mixture
  3. extractionThe separated aqueous layer was extracted with dichloromethane
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (silica gel; dichloromethane/methanol 99:1 )
  9. customThe eluent of the desired fraction was evaporated
  10. customthe residue was crystallized from 2,2'-oxybispropane
  11. filtrationThe crystallized product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-bb8a63fe9e084b9c9475e16def174d7a
Source dataset
uspto-grants-1995_04
Patent number
US05407961

Reaction notes

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