Chlorosuccinimide → HCID 66692113, compound

HRID 1911291Notes

Reaction equation

HRID 1911291 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:12][C:13]#[CH:14])([CH3:4])([CH3:3])[CH3:2].[Cl:15]N1C(=O)CCC1=O>CC(C)=O.C([O-])(=O)C.[Ag+]>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:12][C:13]#[C:14][Cl:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 61343954HCID 61343954, compound

Product 1

HCID 66692113HCID 66692113, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 180AcetoneSolvent

Procedure

To a solution of Example 100A (22.2 g, 118 mmol) in acetone (300 mL) was added N-chlorosuccinimide (18.8 g, 141 mmol) and silver acetate (1.96 g, 11.7 mmol). The reaction was heated to reflux for 24 h, cooled, and the solvent removed by evaporation. The residue was taken up in a mixture of water (125 mL) and diethyl ether (125 mL), and filtered to remove the undissolved silver salts. The filtrate was extracted with diethyl ether (150 mL), and the combined organic layers washed with brine (75 mL) and concentrated to produce 26.9 g of the crude title compound which was used without further purification. MS (DCI/NH3) m/z 240 (M+NH4)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 24 h
  3. temperaturecooled
  4. customthe solvent removed by evaporation
  5. additionThe residue was taken up in a mixture of water (125 mL) and diethyl ether (125 mL)
  6. filtrationfiltered
  7. customto remove the undissolved silver salts
  8. extractionThe filtrate was extracted with diethyl ether (150 mL)
  9. washthe combined organic layers washed with brine (75 mL)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-89d9610e390e4c3e9853ed9366709ee9
Source dataset
uspto-grants-2013_12
Patent number
US08604053B2

Reaction notes

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