Acryloyl chloride → HCID 18959639, compound

HRID 1708608Notes

Reaction equation

HRID 1708608 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[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH3:28])[C:20]=3[CH3:29])/[CH3:18])/[C:9]2=[O:30])=[CH:4][CH:3]=1.[C:31](Cl)(=[O:34])[CH:32]=[CH2:33]>ClCCl>[C:31]([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[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH3:28])[C:20]=3[CH3:29])/[CH3:18])/[C:9]2=[O:30])=[CH:4][CH:3]=1)(=[O:34])[CH:32]=[CH2:33]

Participants

4

Reactant 2

HCID 13140Acryloyl chlorideHCID 18959648HCID 18959648, compound

Product 1

HCID 18959639HCID 18959639, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution obtained by dissolving 1.2 g of N-(4-hydroxyphenyl)-2-[(E)-1-(1,2-dimethyl-3-indolyl)ethylidene]-3-isopropylidenesuccinimide obtained in Example 16 in 25 ml of dichloromethane, followed by dropwise addition of 0.36 ml of acryloyl chloride in 10 minutes. The reaction was carried out at room temperature for additional 30 minutes with stirring. After the reaction, the reaction solution was well washed with water, dried over anhydrous magnesium sulfate, followed by 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-acryloyloxyphenyl)-2-[(E)-1-(1,2-dimethyl-3-indolyl)ethylidene]-3-isopropylidenesuccinimide in yield of 88.5%.

Workup

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

Sources & evidence

ORD record
ord-36282e40391f47dba915739335ea4ebd
Source dataset
uspto-grants-1994_10
Patent number
US05359085

Reaction notes

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