Hydrogen Peroxide → Methyl 2-chloracetamidoacrylate N-acryloamidomethyl 2-oxopyrrolidine

HRID 1722989Notes

Reaction equation

[Cl:1][CH2:2][C:3]([NH:5][C:6](=[CH2:11])[C:7]([O:9][CH3:10])=[O:8])=[O:4].[C:12]([NH:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][C:19]1=[O:23])(=[O:15])[CH:13]=[CH2:14].OO>CO>[Cl:1][CH2:2][C:3]([NH:5][C:6](=[CH2:11])[C:7]([O:9][CH3:10])=[O:8])=[O:4].[C:12]([NH:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][C:19]1=[O:23])(=[O:15])[CH:13]=[CH2:14]

Participants

Conditions

Temperature: 50 °C

Procedure

93.8 g of methyl 2-chloracetamidoacrylate, 31.2 g of N-acrylamidomethyl-2-oxopyrrolidine, 3.5 l. of methanol and 50 g of a 33% hydrogen peroxide solution are placed in a 4 l. photochemical reactor equipped with a 2000 W type Q 2020 original Hanau-type lamp. The solution is heated to 50° C. and irradiated for 6 hours. The reaction mixture is then filtered and the solution is concentrated to 400 g and poured into 5 l. of ethyl ether. The resulting 93 g of polymer is then dried. The water-soluble fraction is extracted with 1.8 l. of water at 50° C. 68 g of water-soluble polymer are obtained.

Workup

customphotochemical reactor equipped with a 2000 W type Q 2020 original Hanau-type lamp
customirradiated for 6 hours
filtrationThe reaction mixture is then filtered
concentrationthe solution is concentrated to 400 g
additionpoured into 5 l
dry with materialThe resulting 93 g of polymer is then dried
extractionThe water-soluble fraction is extracted with 1.8 l
customat 50° C
custom68 g of water-soluble polymer are obtained

Sources & evidence

ORD record: ord-1acde478805541fd9776c6aeb1e4f2d3
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04859460

Reaction notes

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