Methacrylic Acid → N-(Methacryloyloxy)succinimide

HRID 1388110Notes

Reaction equation

HRID 1388110 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].O[N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=[O:14].C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[CH3:3][C:2]([C:1]([O:6][N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=[O:14])=[O:5])=[CH2:4]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 10130244N-(Methacryloyloxy)succinimideYield 71.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 20 ml of acetonitrile were dissolved methacrylic acid (1.72 g, 20 m mols) and N-hydroxysuccinimide (2.19 g, 19 m mols), and under ice-cooling, N,N'-dicyclohexylcarbodiimide (4.33 g, 21 m mols) was added. The reaction was conducted in the dark, at 0° C. for one hour and at room temperature for 3 hours. The precipitate was separated by filtration and the filtrate was distilled under reduced pressure. To the residue was added petroleum ether and, after cooling, the crystals were collected by filtration. By the above procedure there was obtained 2.5 g of methacrylic acid N-hydroxysuccinimide ester as crystals melting at 100°-102° C.

Workup

  1. temperatureunder ice-cooling
  2. customat 0° C.
  3. customfor one hour
  4. customThe precipitate was separated by filtration
  5. distillationthe filtrate was distilled under reduced pressure
  6. additionTo the residue was added petroleum ether
  7. temperatureafter cooling
  8. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-0f09fd0bb6c24404afa55a8ac196d2b2
Source dataset
uspto-grants-1984_02
Patent number
US04430265

Reaction notes

Loading…