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

HRID 1975890Notes

Reaction equation

HRID 1975890 reaction equation
[C:1]([C:5]1[C:6]([NH:8][C:9](=[O:11])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:12]12[CH2:19][CH2:18][CH:15]([CH:16]=[CH:17]1)[CH2:14][CH:13]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[CH:27]12[CH2:33][CH:30]([CH:31]=[CH:32]1)[CH2:29][CH:28]2[C:34]([O:36][CH2:37][CH2:38][OH:39])=[O:35].N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCCC1>[C:1]([C:5]1[C:6]([NH:8][C:9](=[O:11])[CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[CH:12]12[CH2:19][CH2:18][CH:15]([CH:16]=[CH:17]1)[CH2:14][CH:13]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[CH:27]12[CH2:33][CH:30]([CH:31]=[CH:32]1)[CH2:29][CH:28]2[C:34]([O:36][CH2:37][CH2:38][OH:39])=[O:35]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 120338232-Hydroxyethyl bicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 122294171H-Pyrrole-2,5-dione, 3-(1,1-dimethylethyl)-HCID 18413667t-Butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate

Product 1

HCID 86756648t-Butyl maleimide t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate 2-hydroxyethyl 5-norbornene-2-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

t-butyl maleimide (1 mol.), t-butyl bicyclo[2,2,2]oct-5-ene-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) 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(t-butyl maleimide/t-butyl bicyclo[2,2,2]oct-5-ene-2-carboxylate/2-hydroxyethyl 5-norbornene-2-carboxylate) polymer was obtained at a yield of about 75%.

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 75%

Sources & evidence

ORD record
ord-72426b4d5d1e41fbb872ff127f53c17f
Source dataset
uspto-grants-2001_05
Patent number
US06225020B1

Reaction notes

Loading…