Acetone → n-[1-Eth-(z)-ylidene-2,5-dioxo-pentyl]-acrylimidoyl bromide

HRID 2196856Notes

Reaction equation

HRID 2196856 reaction equation
[CH:1](=[C:3](/[N:13]=[C:14]([Br:17])[CH:15]=[CH2:16])\[C:4](=[O:12])[CH2:5][CH2:6][CH:7](OC)[O:8]C)/[CH3:2].CC(C)=O>O>[CH:1](=[C:3](/[N:13]=[C:14]([Br:17])[CH:15]=[CH2:16])\[C:4](=[O:12])[CH2:5][CH2:6][CH:7]=[O:8])/[CH3:2]

Participants

4

Reactant 2

HCID 180AcetoneHCID 87233323n-[1-Eth-(z)-ylidene-5,5-dimethoxy-2-oxo-pentyl]acrylimidoyl bromide

Product 1

HCID 87233280n-[1-Eth-(z)-ylidene-2,5-dioxo-pentyl]-acrylimidoyl bromideYield 88.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of N-[1-Eth-(Z)-ylidene-5,5-dimethoxy-2-oxo-pentyl]acrylimidoyl bromide (7.0 g, 28.9 mmol) in a solution of acetone (30 mL) and water (1.5 mL) at room temperature, is added Amberlyse-15 (20 g). After mechanical shacking for 3 hr at room temperature, the reaction mixture is filtered. The resin beads were washed with acetone (contain 10% of Et3N). The combined organic layers were concentrated and purified by chromatography (Hexane/EtOAc:70/30) to yield N-[1-Eth-(Z)-ylidene-2,5-dioxo-pentyl]-acrylimidoyl bromide (5.18 g, 88.1%) as light yellow liquid. M/Z=421, 243.9 [M+1]

Workup

  1. filtrationthe reaction mixture is filtered
  2. washThe resin beads were washed with acetone (contain 10% of Et3N)
  3. concentrationThe combined organic layers were concentrated
  4. custompurified by chromatography (Hexane/EtOAc:70/30)

Sources & evidence

ORD record
ord-638576a9503a43459933515214a51999
Source dataset
uspto-grants-2012_12
Patent number
US08338440B2

Reaction notes

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