Acetone → MAU N,N-dimethylaminopropylacrylamide methyl chloride

HRID 405661Notes

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].[CH3:20][Cl:21].[CH3:22][NH:23][N:24]([NH:32][CH3:33])[C:25](=[O:31])[C:26]([CH2:28][CH2:29][CH3:30])=[CH2:27].CC(C)=O>CO.N(C(C)(C)C#N)=NC(C)(C)C#N>[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].[CH3:20][Cl:21].[CH3:22][NH:23][N:24]([NH:32][CH3:33])[C:25](=[O:31])[C:26]([CH2:28][CH2:29][CH3:30])=[CH2:27]

Participants

Conditions

Temperature: 60 °C

Procedure

In 59.69 g of methanol were dissolved 18.43 g (68.43 mmol) of 11-methacrylamidoundecanoic acid (MAU), 1.57 g (7.60 mmol) of N,N-dimethylaminopropylacrylamide methyl chloride (Kohjin Co., Ltd.), and 0.31 g (1.89 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 obtained solution was dropwise added into a large excess of acetone, and the resulting precipitate was collected by filtration under suction. After drying under reduced pressure, 9.60 g of random MAU/N,N-dimethylaminopropylacrylamide methyl chloride copolymer (90/10) was obtained (yield: 48.0%). The weight average molecular weight was 42000.

Workup

customby bubbling nitrogen for 60 minutes
customAfter the completion of the polymerization reaction
filtrationthe resulting precipitate was collected by filtration under suction
customAfter drying under reduced pressure

Sources & evidence

ORD record: ord-68e46679b516439bb09a5181474dc5c2
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08753686B2

Reaction notes

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