Acetoxyacetyl chloride → HCID 59824365, compound

HRID 1645491Notes

Reaction equation

HRID 1645491 reaction equation
[NH2:1][C:2]1[C:3]([I:22])=[C:4]([C:8]([I:21])=[C:9]([C:12](=[O:20])[N:13]([CH2:17][CH:18]=[CH2:19])[CH2:14][CH:15]=[CH2:16])[C:10]=1[I:11])[C:5]([Cl:7])=[O:6].[C:23]([O:26][CH2:27][C:28](Cl)=[O:29])(=[O:25])[CH3:24]>C(Cl)Cl>[Cl:7][C:5]([C:4]1[C:3]([I:22])=[C:2]([NH:1][C:28]([CH2:27][O:26][C:23](=[O:25])[CH3:24])=[O:29])[C:10]([I:11])=[C:9]([C:12](=[O:20])[N:13]([CH2:14][CH:15]=[CH2:16])[CH2:17][CH:18]=[CH2:19])[C:8]=1[I:21])=[O:6]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 57583237HCID 57583237, compound

Product 1

HCID 59824365HCID 59824365, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

The mono-diallylamide (9) (6.56 g, 10 mmol) was dissolved in anhydrous DCM (10 ml), and stirred. The acetoxy acetyl chloride (2.1 ml, 20 mmol) was added to the solution, and heated to 40° C. for 3 days. The solvent was removed at reduced pressure and the reaction mixture was absorbed onto silica gel. The crude mixture was separated by silica gel chromatography 10% EtOAc/Petrol=>100% EtOAc over 11 CVs. The main peak was collected, concentrated at reduced pressure and analysed by both LCMS (m/z 756.83 (+ve) and NMR. This indicated the desired material had been made in good purity. The yield was 6.5 g (86%).

Workup

  1. customThe solvent was removed at reduced pressure
  2. customthe reaction mixture was absorbed onto silica gel
  3. customThe crude mixture was separated by silica gel chromatography 10% EtOAc/Petrol=>100% EtOAc over 11 CVs
  4. customThe main peak was collected
  5. concentrationconcentrated at reduced pressure and analysed by both LCMS (m/z 756.83 (+ve) and NMR

Sources & evidence

ORD record
ord-c23ac665a0ff4f0b8d218ddd6742721f
Source dataset
uspto-grants-2012_02
Patent number
US08124806B2

Reaction notes

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