Azobisisobutyronitrile → Ethyl maleimide t-butyl 5-norbornene-2-carboxylate 2-hydroxyethyl 5-norbornene-2-carboxylate

HRID 1975888Notes

Reaction equation

HRID 1975888 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[CH2:16][CH:13]([CH:14]=[CH:15]1)[CH2:12][CH:11]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[CH:24]12[CH2:30][CH:27]([CH:28]=[CH:29]1)[CH2:26][CH:25]2[C:31]([O:33][CH2:34][CH2:35][OH:36])=[O:32].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[CH2:16][CH:13]([CH:14]=[CH:15]1)[CH2:12][CH:11]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[CH:24]12[CH2:30][CH:27]([CH:28]=[CH:29]1)[CH2:26][CH:25]2[C:31]([O:33][CH2:34][CH2:35][OH:36])=[O:32]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 120338232-Hydroxyethyl bicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 14671028Ethyl maleimideHCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl ester

Product 1

HCID 86756646Ethyl maleimide t-butyl 5-norbornene-2-carboxylate 2-hydroxyethyl 5-norbornene-2-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl maleimide (1 mol.), t-butyl 5-norbornene-2-carboxylate (0.5 mol.) and 2-hydroxyethyl 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 5-norbornene-2-carboxylate/2-hydroxyethyl 5-norbornene-2-carboxylate) polymer was obtained at a yield of about 85%. NMR spectra of the polymer is illustrated in FIG. 2.

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 85%

Sources & evidence

ORD record
ord-20a44e61cd5840c099fe97ad0dcfd5e1
Source dataset
uspto-grants-2001_05
Patent number
US06225020B1

Reaction notes

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