Methanol → Maleimide styrene

HRID 1361341Notes

Reaction equation

HRID 1361341 reaction equation
[CH2:1]([N:3](CC)[CH2:4][CH3:5])[CH3:2].ClC([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.[OH2:30].C[OH:32]>CN1CCCC1=O>[C:1]1(=[O:32])[NH:3][C:4](=[O:30])[CH:5]=[CH:2]1.[CH2:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8471TriethylamineHCID 723620523,4-Difluoro-benzoic acid 4-(2-chlorocarbonyl-vinyl)-phenyl ester2×

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), cooled to 0° C., added with 3.291 g (32.52 mmol) of triethylamine (Et3N), stirred for 30 min, added with 6.995 g (21.679 mmol) of (1) 3,4-difluoro-benzoic acid 4-(2-chlorocarbonyl-vinyl)-phenyl ester, and then stirred at room temperature for 4 hours. The reaction solution was poured into water and methanol, after which the resulting solid was filtered. The solid was washed several times with water and then vacuum dried, thus obtaining the desired compound (2) (about 60% yield).

Workup

  1. stirringstirred at room temperature for 4 hours
  2. filtrationafter which the resulting solid was filtered
  3. washThe solid was washed several times with water
  4. customvacuum dried

Sources & evidence

ORD record
ord-3660d5b6f71e424ea7e264dbc9053d42
Source dataset
uspto-grants-2011_02
Patent number
US07879951B2

Reaction notes

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