Triethylamine → HCID 86748205, compound

HRID 1708604Notes

Reaction equation

HRID 1708604 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11](=[C:14]([CH3:16])[CH3:15])/[C:10](=[C:17](\[C:19]3[CH:23]=[C:22]([CH3:24])[O:21][C:20]=3[CH3:25])/[CH3:18])/[C:9]2=[O:26])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:34](Cl)(=[O:37])[CH:35]=[CH2:36]>ClCCl>[C:34]([O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11](=[C:14]([CH3:16])[CH3:15])/[C:10](=[C:17](\[C:19]3[CH:23]=[C:22]([CH3:24])[O:21][C:20]=3[CH3:25])/[CH3:18])/[C:9]2=[O:26])=[CH:4][CH:3]=1)(=[O:37])[CH:35]=[CH2:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 86748206HCID 86748206, compound

Product 1

HCID 86748205HCID 86748205, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution obtained by dissolving 211 mg of N-(4-hydroxyphenyl)-2-[(E)-1-(2,5-dimethyl-3-furyl)ethylidene]-3-isopropylidenesuccinimide obtained in Example 5 in 5 ml of dichloromethane, 72 mg of triethylamine was added, followed by dropwise addition of 66 mg of acryloyl chloride in 10 minutes. The reaction was carried out at room temperature for 30 minutes with stirring. After the reaction, the reaction solution was well washed with water, dried over anhydrous magnesium sulfate, and subjected to removal of the solvent by distillation. The resulting residue was purified by column chromatography (filler: Wakogel C-300, eluent: a mixed solvent of n-hexane and ethyl acetate) to give pale red crystals of N-(4-acryloyloxyphenyl)-2-[(E)-1-(2,5-dimethyl-3-furyl)ethylidene]-3-isopropylidenesuccinimide in yield of 44.0%.

Workup

  1. customTo a solution obtained
  2. additionwas added
  3. customAfter the reaction
  4. washthe reaction solution was well washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customsubjected to removal of the solvent by distillation
  7. customThe resulting residue was purified by column chromatography (filler

Sources & evidence

ORD record
ord-ba6c23e6ace44815abd9520f8e4f93ef
Source dataset
uspto-grants-1994_10
Patent number
US05359085

Reaction notes

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