Methacryloyl chloride → HCID 86748207, compound

HRID 1708606Notes

Reaction equation

HRID 1708606 reaction equation
[NH2:1][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:27](Cl)(=[O:31])[C:28]([CH3:30])=[CH2:29]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:27]([NH: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:31])[C:28]([CH3:30])=[CH2:29]

Participants

5

Reactant 2

HCID 13528Methacryloyl chlorideHCID 86748208HCID 86748208, compound

Product 1

HCID 86748207HCID 86748207, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

To a solution obtained by dissolving 105 mg of N-(4-aminophenyl)-2-[(E)-1-(2,5-dimethyl-3-furyl)ethylidene]-3-isopropylidenesuccinimide obtained in Example 1 in 2 ml of chloroform, 5 ml of pyridine was added, followed by dropwise addition of 0.84 ml of methacryloyl chloride in 10 minutes. The reaction was carried out at room temperature for additional 4 hours with stirring. After the reaction, the reaction solution was well washed with water, dried over anhydrous magnesium sulfate, and subjected to the 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 yellow crystals of N-(4-methacryloylaminophenyl)-2-[(E)-1-(2,5-dimethyl-3-furyl)ethyliden]-3-isopropylidenesuccinimide in yield of 40.0%.

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 the removal of the solvent by distillation
  7. customThe resulting residue was purified by column chromatography (filler

Sources & evidence

ORD record
ord-a27b86cd3ae24918aeb72516a4c17e35
Source dataset
uspto-grants-1994_10
Patent number
US05359085

Reaction notes

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