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Azobisisobutyronitrile → Propyl maleimide t-butyl 5-norbornene-2-carboxylate 2-hydroxyethyl bicyclo[2,2,2]oct-5-ene-2-carboxylate

HRID 1975892
Notes
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Reaction equation

HRID 1975892 reaction equation
[CH2:1]([C:4]1[C:5]([NH:7][C:8](=[O:10])[CH:9]=1)=[O:6])[CH2:2][CH3:3].[CH:11]12[CH2:17][CH:14]([CH:15]=[CH:16]1)[CH2:13][CH:12]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[CH:25]12[CH2:32][CH2:31][CH:28]([CH:29]=[CH:30]1)[CH2:27][CH:26]2[C:33]([O:35][CH2:36][CH2:37][OH:38])=[O:34].N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCCC1>[CH2:1]([C:4]1[C:5]([NH:7][C:8](=[O:10])[CH:9]=1)=[O:6])[CH2:2][CH3:3].[CH:11]12[CH2:17][CH:14]([CH:15]=[CH:16]1)[CH2:13][CH:12]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[CH:25]12[CH2:32][CH2:31][CH:28]([CH:29]=[CH:30]1)[CH2:27][CH:26]2[C:33]([O:35][CH2:36][CH2:37][OH:38])=[O:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterHCID 184136662-Hydroxyethyl bicyclo[2,2,2]oct-5-ene-2-carboxylateHCID 21880478Propyl maleimide

Product 1

HCID 86756650Propyl maleimide t-butyl 5-norbornene-2-carboxylate 2-hydroxyethyl bicyclo[2,2,2]oct-5-ene-2-carboxylate
Yield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Propyl maleimide (1 mol.), t-butyl 5-norbornene-2-carboxylate (0.5 mol.) and 2-hydroxyethyl bicyclo[2,2,2]oct-5-ene-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(propyl maleimide/t-butyl 5-norbornene-2-carboxylate/2-hydroxyethyl bicyclo[2,2,2]oct-5-ene-2-carboxylate) polymer was obtained at a yield of about 79%.

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 79%

Sources & evidence

ORD record
ord-2030d416a3724060b71fe12ef757e3f0
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06225020B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes