Methanol → Maleimide styrene

HRID 901821Notes

Reaction equation

HRID 901821 reaction equation
C([N:3](CC)CC)C.Cl[C:9]([CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][C:16](OC(=O)C2C=CC(F)=C(F)C=2)=[CH:15][CH:14]=1)=[O:10].[CH3:30][OH:31]>CN1CCCC1=O>[C:9]1(=[O:10])[NH:3][C:30](=[O:31])[CH:12]=[CH:11]1.[CH2:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 723620523,4-Difluoro-benzoic acid 4-(2-chlorocarbonyl-vinyl)-phenyl ester

Product 1

HCID 66643759Maleimide styreneYield 60%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

2.74 g (9.033 mmol) of polyhydroxymaleimide-polyhydroxystyrene was dissolved in 50 ml of N-methylpyrrolidone (NMP). After the solution was cooled to 0° C., 3.291 g (32.52 mmol) of triethylamine (Et3N) was added thereto. The mixture was stirred for 30 minutes. 6.995 g (21.679 mmol) of 3,4-difluoro-benzoic acid 4-(2-chlorocarbonyl-vinyl)-phenyl ester was added to the mixture and stirred at room temperature for 4 hours. The reaction solution was poured into an aqueous solution of methanol, and filtered to obtain a solid. The solid was washed with water several times and dried in vacuo, affording the desired compound 2 (yield: 60%).

Workup

  1. stirringstirred at room temperature for 4 hours
  2. filtrationfiltered
  3. customto obtain a solid
  4. washThe solid was washed with water several times
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8bf9b2300d3d4e90bbec29196bf30c07
Source dataset
uspto-grants-2008_04
Patent number
US07364940B2

Reaction notes

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