Azobisisobutyronitrile → Ethyl maleimide t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate 3-hydroxypropyl 5-norbornene-2-carboxylate

HRID 1975891Notes

Reaction equation

HRID 1975891 reaction equation
[CH2:1]([C:3]1[C:4]([NH:6][C:7](=[O:9])[CH:8]=1)=[O:5])[CH3:2].[CH:10]12[CH2:17][CH2:16][CH:13]([CH:14]=[CH:15]1)[CH2:12][CH:11]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[CH:25]12[CH2:31][CH:28]([CH:29]=[CH:30]1)[CH2:27][CH:26]2[C:32]([O:34][CH2:35][CH2:36][CH2:37][OH:38])=[O:33].N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCCC1>[CH2:1]([C:3]1[C:4]([NH:6][C:7](=[O:9])[CH:8]=1)=[O:5])[CH3:2].[CH:10]12[CH2:17][CH2:16][CH:13]([CH:14]=[CH:15]1)[CH2:12][CH:11]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[CH:25]12[CH2:31][CH:28]([CH:29]=[CH:30]1)[CH2:27][CH:26]2[C:32]([O:34][CH2:35][CH2:36][CH2:37][OH:38])=[O:33]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 14671028Ethyl maleimideHCID 18413667t-Butyl bicyclo[2,2,2]oct-5-ene-2-carboxylateHCID 235020283-Hydroxypropyl 5-norbomene-2-carboxylate

Product 1

HCID 86756649Ethyl maleimide t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate 3-hydroxypropyl 5-norbornene-2-carboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl maleimide (1 mol.), t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate (0.5 mol.) and 3-hydroxypropyl 5-norbornene-2-carboxylate (0.5 mol) were dissolved in 50 g to 300 g of tetrahydrofuran (THF), 2 g to 15 g of 2,2′-azobisisobutyronitrile (AIBN) was added thereto, and the resulting solution was reacted at a temperature between 60° C. and 70° C. in a nitrogen atmosphere for 10 hours. After a high molecular weight was achieved by the reaction, the resultant product was precipitated in an ethyl ether or hexane solvent. The gathered precipitate was dried, and the desired poly(ethyl maleimide/t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate/3-hydroxypropyl 5-norbornene-2-carboxylate) polymer was obtained at a yield of about 83%. NMR spectra of the polymer is illustrated in FIG. 4.

Workup

  1. customthe resulting solution was reacted at a temperature between 60° C. and 70° C. in a nitrogen atmosphere for 10 hours
  2. customAfter a high molecular weight was achieved by the reaction
  3. customthe resultant product was precipitated in an ethyl ether or hexane solvent
  4. customThe gathered precipitate was dried
  5. customwas obtained at a yield of about 83%

Sources & evidence

ORD record
ord-8075e20c3660497d8f10866387ef1c38
Source dataset
uspto-grants-2001_05
Patent number
US06225020B1

Reaction notes

Loading…