Chlorosuccinimide → HCID 21946116, compound

HRID 1047347Notes

Reaction equation

HRID 1047347 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-5ffdaa07dd904e7a96a841f60af7f3d6
Source dataset
uspto-grants-2013_10
Patent number
US08569516B2

Reaction notes

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