Phenol → N-Phenylmaleimide

HRID 2163129Notes

Reaction equation

HRID 2163129 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([N:7]=[C:8]2[O:13][C:11](=[O:12])[CH:10]=[CH:9]2)=[CH:3][CH:2]=1.C1(O)C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl>[C:4]1([N:7]2[C:11](=[O:12])[CH:10]=[CH:9][C:8]2=[O:13])[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 8471TriethylamineHCID 2608105-(Phenylimino)furan-2(5H)-one

Product 1

HCID 13662N-PhenylmaleimideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

10 g (0.058mole) of N-phenyl isomaleimide is dissolved in 100 ml of methylene chloride. To the solution are added 0.400 g (0.004 mole) of phenol and 0.4 ml (0.290 g; 0.0029 mole) of triethylamine. The reaction mixture is stirred at 20-25° C. for 3 hours, and is then extracted by shaking twice with 10% aqueous NaOH solution; it is washed twice with water, dried over sodium sulphate and the solvent is removed in a rotary evaporator. The residue is dried at 40° C. in vacuo to obtain 9.7 g (97% of theory) of yellow crystalline N-phenyl maleimide, m.p. 85-86° C.

Workup

  1. extractionis then extracted
  2. stirringby shaking twice with 10% aqueous NaOH solution
  3. washit is washed twice with water
  4. dry with materialdried over sodium sulphate
  5. customthe solvent is removed in a rotary evaporator
  6. customThe residue is dried at 40° C. in vacuo

Sources & evidence

ORD record
ord-eddfbbfef627498cbf4dc7ba510b7ada
Source dataset
uspto-grants-1979_01
Patent number
US04132715

Reaction notes

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