Acetyl chloride → HCID 82341151, compound

HRID 2416963Notes

Reaction equation

HRID 2416963 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[CH3:13])(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:18](Cl)(=[O:20])[CH3:19]>C(=S)=S>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:18](=[O:20])[CH3:19])=[CH:10][CH:11]=2)[CH2:6][CH:5]1[CH3:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 43082211-(2-Methyl-2,3-dihydroindol-1-yl)ethanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 82341151HCID 82341151, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of the compound from Step 1 (2.0 g, 11.4 mmol) and aluminum chloride (7.0 g, 52 mmol) in carbon disulfide (20 mL) is added acetyl chloride (1.2 mL, 17.1 mmol). The mixture is heated at 50° C. for 72 h, cooled, quenched with ice water then diluted with ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate, filtered, concentrated, and chromatographed on silica gel eluting with 40-50% ethyl acetate in heptane to give 2.4 g (97%) of the title compound as a off-white solid. MS (ESI+) m/z 217.1 (M+H). Anal. Calcd for C13H15NO2: C, 71.87; H, 6.96; N, 6.45. Found: C, 71.78; H, 6.98; N, 6.43.

Workup

  1. temperaturecooled
  2. customquenched with ice water
  3. additionthen diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel eluting with 40-50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-28bcfb869d4c4e0d9ad021bf686eb8b8
Source dataset
uspto-grants-2004_11
Patent number
US06825225B2

Reaction notes

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