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Azobisisobutyronitrile → MAU 2-(N,N-dimethylamino)ethyl acrylate

HRID 405657
Notes
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Reaction equation

HRID 405657 reaction equation
[C:1]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:20]([O:24][CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])(=[O:23])[CH:21]=[CH2:22].N(C(C)(C)C#N)=NC(C)(C)C#N>CO>[C:1]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:20]([O:24][CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])(=[O:23])[CH:21]=[CH2:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 171112-(Dimethylamino)ethyl acrylateHCID 276418511-(Methacryloylamino)undecanoic acid

Product 1

HCID 131731616MAU 2-(N,N-dimethylamino)ethyl acrylateYield 162.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In 59.68 g of methanol were dissolved 18.88 g (70.12 mmol) of 11-methacrylamidoundecanoic acid (MAU), 1.12 g (7.79 mmol) of 2-(N,N-dimethylamino)ethyl acrylate (Tokyo Chemical industry Co.), and 0.32 g (1.95 mmol) of azobisisobutyronitrile (Nacalai Tesque, Inc.). The solution was deaerated by bubbling nitrogen for 60 minutes. The container was covered with a septum, and the polymerization was conducted by heating at 60° C. for 20 hours. After the completion of the polymerization reaction, the solution was concentrated to dryness under reduced pressure, and the solid was dissolved in 60 g of dimethylformamide. The obtained solution was dropwise added into a large excess of diethyl ether, and the resulting precipitate was collected by filtration under suction. After drying under reduced pressure, 5.22 g of random MAU/2-(N,N-dimethylamino)ethyl acrylate copolymer (90/10) was obtained (yield: 26.1%). The weight average molecular weight was 130000.

Workup

  1. customby bubbling nitrogen for 60 minutes
  2. customAfter the completion of the polymerization reaction
  3. concentrationthe solution was concentrated to dryness under reduced pressure
  4. dissolutionthe solid was dissolved in 60 g of dimethylformamide
  5. additionThe obtained solution was dropwise added into a large excess of diethyl ether
  6. filtrationthe resulting precipitate was collected by filtration under suction
  7. customAfter drying under reduced pressure

Sources & evidence

ORD record
ord-37264b3a59d0413da954ad40b551bd50
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08753686B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes