Acetone → MAU N,N-dimethylaminoethyl acrylate methyl chloride

HRID 405660

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].[C:22]([O:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])(=[O:25])[CH:23]=[CH2:24].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].[C:22]([O:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])(=[O:25])[CH:23]=[CH2:24]

Participants

Conditions

Temperature: 60 °C

Procedure

In 59.69 g of methanol were dissolved 18.52 g (68.77 mmol) of 11-methacrylamidoundecanoic acid (MAU), 1.48 g (7.64 mmol) of N,N-dimethylaminoethyl acrylate 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, 9.43 g of random MAU/N,N-dimethylaminoethyl acrylate methyl chloride copolymer (90/10) was obtained (yield: 47.2%). The weight average molecular weight was 68000.

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-d3c3d716cd464371a9eb4951320aa495
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08753686B2

Linked notes

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