Methacrylic anhydride → 2-[Ethyl(phenyl)amino]ethyl prop-2-enoate

HRID 519257Notes

Reaction equation

HRID 519257 reaction equation
[C:1]([O:6][C:7](=[O:11])[C:8]([CH3:10])=C)(=O)[C:2](C)=C.O[CH2:13][CH2:14][N:15](CC)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[C:7]([O:6][CH2:1][CH2:2][N:15]([CH2:14][CH3:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:11])[CH:8]=[CH2:10]

Participants

4

Reactant 2

HCID 12974Methacrylic anhydrideHCID 623382-(N-ethylanilino)ethanol

Product 1

HCID 190971262-[Ethyl(phenyl)amino]ethyl prop-2-enoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
55 °C

Procedure

Methacrylic anhydride (7.7 g, 0.05 mol) is added to a solution of N-(2-hydroxyethyl)-N-ethylaniline (6.6 g, 0.04 mol) in pyridine (25 ml) and the mixture is stirred at 55° C. for 2 hours. On cooling the mixture is passed through silica gel to give N-(2-acryloyloxyethyl)-N-ethylaniline as a pale yellow oil. 5.3 g, 65%

Workup

  1. temperatureOn cooling the mixture

Sources & evidence

ORD record
ord-b6a855aa18e948d3a1b8c85244d381bf
Source dataset
uspto-grants-2015_08
Patent number
US09115464B2

Reaction notes

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