Triethylamine → HCID 18959650, compound

HRID 1708605Notes

Reaction equation

HRID 1708605 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]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[S:21][C:20]=3[CH3:30])/[CH3:18])/[C:9]2=[O:31])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:39](Cl)(=[O:43])[C:40]([CH3:42])=[CH2:41]>ClCCl>[C:39]([O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11](=[C:14]([CH3:15])[CH3:16])/[C:10](=[C:17](\[C:19]3[CH:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[S:21][C:20]=3[CH3:30])/[CH3:18])/[C:9]2=[O:31])=[CH:4][CH:3]=1)(=[O:43])[C:40]([CH3:42])=[CH2:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 18959649HCID 18959649, compound

Product 1

HCID 18959650HCID 18959650, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution obtained by dissolving 430 mg of N-(4-hydroxyphenyl)-2-[(E)-1-(2-methyl-5-phenyl-3-thienyl)ethylidene]-3-isopropylidenesuccinimide obtained in Example 8 in 10 ml of dichloromethane, 202 mg of triethylamine was added, followed by dropwise addition of 209 mg of methacryloyl chloride in 10 minutes. The reaction was carried out at room temperature for further 1 hour. After the reaction, the reaction solution was 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 solution of n-hexane and ethyl acetate) to give organce crystals of N-(4-methacryloyloxyphenyl)-2-[(E)-1-(2-methyl-5-phenyl-3-thienyl)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 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-103871b1964941669dbf4a0b1ab6ac58
Source dataset
uspto-grants-1994_10
Patent number
US05359085

Reaction notes

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