Acrylamide → Ethyl (acryloylamino)(hydroxy)acetate

Reaction equation

CCOC(O)C(OCC)=O.C(N)(=O)C=C.C([O:18][CH:19]([NH:25][C:26](=[O:29])[CH:27]=[CH2:28])[C:20]([O:22][CH2:23][CH3:24])=[O:21])C>>[C:26]([NH:25][CH:19]([OH:18])[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:29])[CH:27]=[CH2:28]

Participants

Reactant 3

HCID 6579Acrylamide

HCID 95630Ethyl 2-ethoxy-2-hydroxyacetate

HCID 57306758Ethyl Acrylamidoglycolate Ethyl Ether

Product 1

HCID 18997977Ethyl (acryloylamino)(hydroxy)acetate

Procedure

Ethyl glyoxylate hemiacetal obtained from Example A in the amount of 29.5 parts (0.2 mole) is employed along with 14.3 parts (0.2 mole) of acrylamide following the procedure of Example I. The reaction is run at 70°-85° C. for 2.5 hours. Analysis of the product by 13C NMR shows a 90% conversion with a 90% selectivity to ethyl acrylamidoglycolate ethyl ether are also found.

Sources & evidence

ORD record: ord-d8ac2cd86df04edc8cb3f0ae0a704247
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04760168

Reaction notes

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