Azobisisobutyronitrile → 2-Maleimidylethanol maleic anhydride t-butyl 5-norbornene-2-carboxylate 2-hydroxyethyl 5-norbornene-2-carboxylate 5-norbornene-2-carboxylic acid

HRID 1276024Notes

Reaction equation

HRID 1276024 reaction equation
[C:1]1(=[O:10])[N:5]([CH2:6][CH2:7][OH:8])[C:4](=[O:9])[CH:3]=[CH:2]1.[C:11]1(=[O:17])[O:16][C:14](=[O:15])[CH:13]=[CH:12]1.[CH:18]12[CH2:24][CH:21]([CH:22]=[CH:23]1)[CH2:20][CH:19]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C([C:34]12[CH2:40][CH:37]([CH:38]=[CH:39]1)[CH2:36][CH:35]2[C:41]([O:43]O)=[O:42])C.[CH:45]12[CH2:51][CH:48]([CH:49]=[CH:50]1)[CH2:47][CH:46]2[C:52]([OH:54])=[O:53].CC(N=NC(C#N)(C)C)(C#N)C>C1COCC1>[C:4]1(=[O:9])[N:5]([CH2:6][CH2:7][OH:8])[C:1](=[O:10])[CH:2]=[CH:3]1.[C:14]1(=[O:15])[O:16][C:11](=[O:17])[CH:12]=[CH:13]1.[CH:18]12[CH2:24][CH:21]([CH:22]=[CH:23]1)[CH2:20][CH:19]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].[CH:34]12[CH2:40][CH:37]([CH:38]=[CH:39]1)[CH2:36][CH:35]2[C:41]([O:43][CH2:46][CH2:52][OH:53])=[O:42].[CH:45]12[CH2:51][CH:48]([CH:49]=[CH:50]1)[CH2:47][CH:46]2[C:52]([OH:54])=[O:53]

Participants

8

Reactant 6

HCID 6547AzobisisobutyronitrileHCID 7923Maleic AnhydrideHCID 789495-Norbornene-2-carboxylic acidHCID 458487N-(2-Hydroxyethyl)maleimideHCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterHCID 86756137HCID 86756137, compound

Product 1

HCID 867561362-Maleimidylethanol maleic anhydride t-butyl 5-norbornene-2-carboxylate 2-hydroxyethyl 5-norbornene-2-carboxylate 5-norbornene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Maleimidylethanol (12) (0.3 to 1 mol), 0.05 to 1 mol of maleic anhydride, 0.1 to 1 mol of t-butyl 5-norbornene-2-carboxylate (19), 0.05 to 1 mol of 2-hydroxyethyl 5-norbornene-2-carboxylate (21), and 0.01 to 0.3 mol of 5-norbornene-2-carboxylic acid (20) were dissolved in 180 to 230 g of THF to which was added 0.5 to 20 g of AIBN as a polymerization initiator. The reaction mixture was allowed to react at 60° C. to 75° C. for 4 to 24 hours under a nitrogen atmosphere. The resulting crude resin was precipitated with ethyl ether and dried to obtain poly[2-maleimidylethanol/maleic anhydride/t-butyl 5-norbornene- 2-carboxylate/2-hydroxyethyl 5-norbornene-2-carboxylate/5-norbornene-2-carboxylic acid] copolymer resin. The NMR spectral data of the resulting resin is shown in FIG. 6.

Workup

  1. customto react at 60° C. to 75° C. for 4 to 24 hours under a nitrogen atmosphere
  2. customThe resulting crude resin was precipitated with ethyl ether
  3. customdried

Sources & evidence

ORD record
ord-8a8c90a2c8fc4b45a4d58c998c566c79
Source dataset
uspto-grants-2000_12
Patent number
US06165672

Reaction notes

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