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Azobisisobutyronitrile → Propyl maleimide t-butyl 5-norbornene-2-carboxylate 3-hydroxypropyl 5-norbornene-2-carboxylate

HRID 1975889
Notes
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Reaction equation

HRID 1975889 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[CH2:31][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: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[CH2:31][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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterHCID 21880478Propyl maleimideHCID 235020283-Hydroxypropyl 5-norbomene-2-carboxylate

Product 1

HCID 86756647Propyl maleimide t-butyl 5-norbornene-2-carboxylate 3-hydroxypropyl 5-norbornene-2-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Propyl maleimide (1 mol.), t-butyl 5-norbornene-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) were added thereto, then the resultant solution was reacted at a temperature of 60° C. to 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/3-hydroxypropyl 5-norbornene-2-carboxylate) polymer was obtained at a yield of about 82%. NMR spectra of the polymer is illustrated in FIG. 3.

Workup

  1. customAfter a high molecular weight was achieved by the reaction
  2. customthe resultant product was precipitated in an ethyl ether or hexane solvent
  3. customThe gathered precipitate was dried
  4. customwas obtained at a yield of about 82%

Sources & evidence

ORD record
ord-43a23beb0e4e480a8b474e2599a4b5d1
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