Methyl Methacrylate → 2-Propenamide, N,N-bis(2-hydroxyethyl)-2-methyl-

HRID 444584Notes

Reaction equation

HRID 444584 reaction equation
CO[C:3](=[O:7])[C:4]([CH3:6])=[CH2:5].[NH:8]([CH2:12][CH2:13][OH:14])[CH2:9][CH2:10][OH:11]>C[O-].[Na+].O>[OH:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][OH:14])[C:3](=[O:7])[C:4]([CH3:6])=[CH2:5]

Participants

5

Reactant 2

HCID 6658Methyl MethacrylateHCID 8113Diethanolamine

Product 1

HCID 30848892-Propenamide, N,N-bis(2-hydroxyethyl)-2-methyl-

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 962WaterSolvent

Procedure

N,N-bis(2-hydroxyethyl)methacrylamide was prepared by the alcoholysis of methylmethacrylate with diethanolamine in the presence of sodium methoxide catalyst, following the general procedure of Gast, Schneider and Cowen (J. Am. Oil Chem. Soc. 43 418 (1966)). The crude product was stripped of volatile materials in vacuo, and then dissolved in water and treated with a strong acid ion-exchange resin, sold under the trade mark Dowex X 50, to remove unchanged diethanolamine and any basic by-products. After removing the water in a rotary vacuum evaporator, a colourless oil was obtained which was shown by NMR analysis to be the desired compound in a satisfactory state of purity.

Workup

  1. additiontreated with a strong acid ion-exchange resin
  2. customto remove unchanged diethanolamine
  3. customAfter removing the water
  4. customin a rotary vacuum evaporator
  5. customa colourless oil was obtained which

Sources & evidence

ORD record
ord-3f57be43f91a48b994f73849ec0cc114
Source dataset
uspto-grants-1981_04
Patent number
US04264656

Reaction notes

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