Triethylamine → HCID 21879849, compound

HRID 724245Notes

Reaction equation

HRID 724245 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH:5]2[CH2:8][CH:9]([CH3:12])[CH2:10][CH2:11][CH:4]2[C:3]1=[O:13].C(N(CC)CC)C.[C:21](Cl)(=[O:24])[CH:22]=[CH2:23]>ClCCCl>[C:21]([O:1][N:2]1[C:6](=[O:7])[CH:5]2[CH2:8][CH:9]([CH3:12])[CH2:10][CH2:11][CH:4]2[C:3]1=[O:13])(=[O:24])[CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 15593377HCID 15593377, compound

Product 1

HCID 21879849HCID 21879849, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Next, 10.07 g (0.055 mol) of N-hydroxy-4-methylhexahydrophthalimide, 15 ml (0.11 mol) of triethylamine, and 50 ml of 1,2-dichloroethane were poured in a 100 ml flask. Then, 7.2 ml (0.090 mol) of acrylyl chloride was slowly dropped therein at a room temperature under nitrogen with stirring. After the dropping, a mixture thus prepared was reacted for one hour at a room temperature. A reaction mixture was washed with water so as to separate an organic layer therefrom. Then, the organic layer was washed with a 5% sodium hydrogen carbonate aqueous solution. The organic layer separated from the 5% sodium hydrogen carbonate aqueous solution was dried with magnesium sulfate, and then a solvent was removed from the organic layer. 11.8 g of N-(acryloyloxy)-4-methylhexahydrophthalimide (viscous liquid of dark yellow color) was thereby obtained. N-(acryloyloxy)-4-methylhexahydrophthalimide is represented by the following formula (120):

Workup

  1. customAfter the dropping, a mixture thus prepared
  2. customwas reacted for one hour at a room temperature
  3. washA reaction mixture was washed with water so as
  4. customto separate an organic layer
  5. washThen, the organic layer was washed with a 5% sodium hydrogen carbonate aqueous solution
  6. customThe organic layer separated from the 5% sodium hydrogen carbonate aqueous solution
  7. dry with materialwas dried with magnesium sulfate
  8. customa solvent was removed from the organic layer

Sources & evidence

ORD record
ord-8288083a6f8e49ba9c866820e59175d6
Source dataset
uspto-grants-2006_11
Patent number
US07141614B2

Reaction notes

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