3-Chloropropionyl chloride → HCID 13620381, compound

HRID 2041584Notes

Reaction equation

HRID 2041584 reaction equation
[Cl:1][CH2:2][CH2:3][C:4](Cl)=[O:5].[CH3:7][C:8]1([CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17].[Cl-].[Cl-].[Cl-].[Al+3]>C(=S)=S>[Cl:1][CH2:2][CH2:3][C:4]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:17])[C:8]2([CH3:18])[CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13620381HCID 13620381, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Under nitrogen atmosphere, add chloropropionyl chloride (1.54 mL, 16.13 mmol) to a mixture of 3,3-dimethyl-1,3-dihydro-indol-2-one (2.0 g, 12.41 mmol) and aluminium trichloride (10.26 g, 76.92 mmol) in carbon disulphide (70 mL). Heat under reflux for 3 h then allow to cool. Decant off the solvent and replace it carefully with ice/water (200 mL). Allow the resultant suspension to stir for 20 min before filtering off the product and washing with water (80 mL). Dry in vacuo to obtain the desired intermediate as a pale brown solid (3.08 g, 99%).

Workup

  1. temperatureHeat
  2. temperatureunder reflux for 3 h
  3. temperatureto cool
  4. customDecant off the solvent
  5. filtrationbefore filtering off the product
  6. washwashing with water (80 mL)
  7. customDry in vacuo

Sources & evidence

ORD record
ord-fb1d141a8b4a439094802451df6ea34e
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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