Azobisisobutyronitrile → HCID 86756138, compound

HRID 1276025Notes

Reaction equation

HRID 1276025 reaction equation
[C:1]1(=[O:11])[N:5]([CH2:6][CH2:7][CH2:8][OH:9])[C:4](=[O:10])[CH:3]=[CH:2]1.[C:12]1(=[O:18])[O:17][C:15](=[O:16])[CH:14]=[CH:13]1.[CH:19]12[CH2:25][CH:22]([CH:23]=[CH:24]1)[CH2:21][CH:20]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C([C:35]12[CH2:41][CH:38]([CH:39]=[CH:40]1)[CH2:37][CH:36]2[C:42]([O:44]O)=[O:43])C.[CH:46]12[CH2:52][CH:49]([CH:50]=[CH:51]1)[CH2:48][CH:47]2[C:53]([OH:55])=[O:54].CC(N=NC(C#N)(C)C)(C#N)C>C1COCC1>[C:1]1(=[O:11])[N:5]([CH2:6][CH2:7][CH2:8][OH:9])[C:4](=[O:10])[CH:3]=[CH:2]1.[C:15]1(=[O:16])[O:17][C:12](=[O:18])[CH:13]=[CH:14]1.[C:29]([O:28][C:26]([CH:20]1[CH2:21][CH:22]2[CH2:25][CH:19]1[CH:24]=[CH:23]2)=[O:27])([CH3:32])([CH3:30])[CH3:31].[CH:35]12[CH2:41][CH:38]([CH:39]=[CH:40]1)[CH2:37][CH:36]2[C:42]([O:44][CH2:47][CH2:53][OH:54])=[O:43].[CH:46]12[CH2:52][CH:49]([CH:50]=[CH:51]1)[CH2:48][CH:47]2[C:53]([OH:55])=[O:54]

Participants

8

Reactant 6

HCID 6547AzobisisobutyronitrileHCID 7923Maleic AnhydrideHCID 789495-Norbornene-2-carboxylic acidHCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterHCID 22177285N-(3-Hydroxypropyl)maleimideHCID 86756137HCID 86756137, compound

Product 1

HCID 86756138HCID 86756138, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Maleimidylpropanol (13) (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 150 to 250 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 an argon atmosphere. The resulting crude resin was precipitated with hexane and dried to obtain poly[3-maleimidylpropanol/maleic anhydride/t-butyl-5-norbornene-2- carboxylate/2-hydroxyethyl 5- norbornene-2-carboxylate/5-norbornene-2-carboxylic acid] copolymer resin.

Workup

  1. customto react at 60° C. to 75° C. for 4 to 24 hours under an argon atmosphere
  2. customThe resulting crude resin was precipitated with hexane
  3. customdried

Sources & evidence

ORD record
ord-4698dae904b948748071137f5e3a495c
Source dataset
uspto-grants-2000_12
Patent number
US06165672

Reaction notes

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