Azobisisobutyronitrile → HCID 86756132, compound

HRID 1276013Notes

Reaction equation

HRID 1276013 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:9]=[CH2:10].[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[CH:16]=[CH2:17].[C:24]([O:28][CH3:29])(=[O:27])[CH:25]=[CH2:26].N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCCC1>[C:4]1(=[O:5])[O:6][C:1](=[O:7])[CH:2]=[CH:3]1.[CH2:8]([Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:9]=[CH2:10].[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[CH:16]=[CH2:17].[C:24]([O:28][CH3:29])(=[O:27])[CH:25]=[CH2:26]

Participants

7

Reactant 5

HCID 6547AzobisisobutyronitrileHCID 7294Methyl AcrylateHCID 7923Maleic Anhydride2×HCID 15458tert-Butyl acrylateHCID 69808Allyltrimethylsilane

Product 1

HCID 86756132HCID 86756132, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
64 °C

Procedure

In a 250 ml, round bottom flask equipped with a reflux condenser and a gas inlet was combined maleic anhydride (8.85 g, 0.090 mol) and tetrahydrofuran (30 ml). The mixture was stirred under a N2 atmosphere until all the maleic anhydride was dissolved. To this solution was added allyltrimethylsilane (10.29 g, 0.090 mol), t-butyl acrylate (8.76 g, 0.068 mol), methyl acrylate (2.10 g, 0.024 mol) and 2,2'-azobisisobutyronitrile (0.148 g, 0.9 mmol). The mixture was heated to 64° C., and the mixture was stirred at this temperature for 18 h. The reaction mixture was cooled to room temperature and added dropwise to hexanes (500 ml). The precipitate was filtered, and the solid was dried in vacuo (12 mm Hg) at room temperature for 1 h. The solid was dissolved in tetrahydrofuran (50 ml), and the solution was added dropwise to hexanes (500 ml). The precipitate was filtered, and the solid was dried in vacuo (0.2 mm Hg) 50° C. for 16 h giving poly(maleic anhydride-allyltrimethylsilane-t-butyl acrylate-methyl acrylate) (22.6 g, 75.3%) as a white powder. 1H NMR (d6 -acetone, 250 MHz): 30.0 mol % maleic anhydride, 30.0 mol % allyltrimethylsilane, 25.4 mol % t-butyl acrylate, 14.8 mol % methyl acrylate. GPC (Waters Corp. liquid chromatograph [refractive index detection, Millenium GPC V software, Phenogel-10, 7.8×250 mm column: 10-4A, 500A&50A, THF eluent]): Mw =14, 921; Polydispersity=2.51; Rmin =about 0.1 Å/sec.

Workup

  1. customIn a 250 ml, round bottom flask equipped with a reflux condenser and a gas inlet
  2. dissolutionwas dissolved
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationThe precipitate was filtered
  5. customthe solid was dried in vacuo (12 mm Hg) at room temperature for 1 h
  6. dissolutionThe solid was dissolved in tetrahydrofuran (50 ml)
  7. additionthe solution was added dropwise to hexanes (500 ml)
  8. filtrationThe precipitate was filtered
  9. customthe solid was dried in vacuo (0.2 mm Hg) 50° C. for 16 h

Sources & evidence

ORD record
ord-9b9726d1053048ffb7b1d54bd34ed8c3
Source dataset
uspto-grants-2000_12
Patent number
US06165682

Reaction notes

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