Acetone → 4-((3-Methacrylamidopropyl)dimethylammonio)butane-1-sulfonate

HRID 473539

Reaction equation

[CH3:1][N:2]([CH3:12])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:11])[C:8]([CH3:10])=[CH2:9].[CH2:13]1[S:18](=[O:20])(=[O:19])[O:17][CH2:16][CH2:15][CH2:14]1.CC(C)=O.CO>C(#N)C>[S:18]([CH2:13][CH2:14][CH2:15][CH2:16][N+:2]([CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:11])[C:8]([CH3:10])=[CH2:9])([CH3:12])[CH3:1])([O-:17])(=[O:20])=[O:19]

Participants

Conditions

Temperature: 70 °C

Procedure

In 380 ml of acetonitrile were dissolved 130 g (0.764 mol) of N-[3-(dimethylamino)propyl]methacrylamide, 104 g of butanesultone and 234 mg of 4-hydroxy-2,2,6,6-tetramethylpiperidinoxy and the solution was heated at 70° C. for 6 hours. After allowing to cooling, to the reaction mixture were added 1,350 ml of acetone and 150 ml of methanol and the mixture was stirred at room temperature for one hour. The crystals deposited were collected by filtration and thoroughly washed with acetone to obtain 200.0 g (yield: 85%) of 4-sulfonatobutyl[3-(methacryloylamino)propyl]dimethylammonium.

Workup

temperatureto cooling, to the reaction mixture
filtrationThe crystals deposited were collected by filtration
washthoroughly washed with acetone

Sources & evidence

ORD record: ord-d96a2ec609454e248a967f7ae9380428
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637221B2

Linked notes

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