Chlorosuccinimide → HCID 21946116, compound

HRID 488554Notes

Reaction equation

HRID 488554 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12].[Cl:15]N1C(=O)CCC1=O>CO>[Cl:15][C:5]1[C:4]([OH:8])=[C:3]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[C:2]([OH:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 21946142HCID 21946142, compound

Product 1

HCID 21946116HCID 21946116, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 30 (5.0 g, 25.5 mmol) in 50 ml of methanol was added 3.4 g (25.5 mmol) of N-chlorosuccinimide. The reaction was stirred overnight at room temperature and concentrated. The residue was suspended in a mixture of hexane and ethyl acetate and the precipitated succinimide was removed by filtration. Crude product obtained after evaporation of the solvent was chromatographed on silica eluting with 4:1 hexane-ethyl acetate. Concentration of the pure product fractions afforded 4.4 g of the title compound as colorless oil that slowly crystallized during prolonged drying under vacuum. 1H NMR (d6-DMSO) δ: 9.52 (s, 1H), 8.95 (s, 1H), 6.97 (d, J=8.5 Hz, 1H), 6.35 (d, J=8.5 Hz, 1H), 3.59 (s, 3H), 2.81 (t, J=7.5 Hz, 2H), 2.34 (t, J=7.5 Hz, 2H).

Workup

  1. concentrationconcentrated
  2. additionThe residue was suspended in a mixture of hexane and ethyl acetate
  3. customthe precipitated succinimide was removed by filtration
  4. customCrude product obtained
  5. customafter evaporation of the solvent
  6. customwas chromatographed on silica eluting with 4:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-347a327153c2452bb6004e6dc30083d3
Source dataset
uspto-grants-2005_12
Patent number
US06972339B2

Reaction notes

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