Hydrochloric Acid → N-{2-Hydroxy-3-[(2-methylprop-2-enoyl)oxy]propyl}-N-phenylglycine

HRID 483765Notes

Reaction equation

HRID 483765 reaction equation
[Na].[C:2]1([NH:8][CH2:9][C:10]([OH:12])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C=CC(O)=CC=1)O.[C:21]([O:26][CH2:27][CH:28]1[O:30][CH2:29]1)(=[O:25])[C:22]([CH3:24])=[CH2:23].Cl>O.CO>[OH:30][CH:28]([CH2:27][O:26][C:21](=[O:25])[C:22]([CH3:24])=[CH2:23])[CH2:29][N:8]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]([OH:12])=[O:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 7837Glycidyl methacrylateHCID 66025N-PhenylglycineHCID 5360545Sodium

Product 1

HCID 94302N-{2-Hydroxy-3-[(2-methylprop-2-enoyl)oxy]propyl}-N-phenylglycine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A sodium salt of N-phenylglycine of 50 g (0.29 mol) was dissolved in water of 50 g and methanol of 50 g and then hydroquinone of 18 mg were added to the resulting solution. This solution was heated up to temperatures of 45° to 50° C. and glycidyl methacrylate of 41 g (0.29 mol) was added dropwise for 20 minutes with stirring followed by stirring for further 2 hours. Water of 200 g was added to the resulting solution and acidified with hydrochloric acid followed by filtering and drying the resulting crystals. N-(2-hydroxy-3-methacryloxypropyl)-N-phenylglycine (hereinafter called GMA-NPG for short) of 45 g was obtained. Then GMA-NPG of 2.0 g, MMA (methyl methacrylate) of 14.0 g, EA (ethyl acrylate) of 2.4 g and MAA (methacrylic acid) of 1.6 g were dissolved in dimethylformamide of 80 g. 20 g of a 1 wt %-solution of benzoyl peroxide in dimethylformamide was added dropwise to the above described solution under an atmosphere of nitrogen at 70° C. followed by stirring for further 6 hours. After cooling, hexane of about 10 times in weight was added to dilute the solution, the resulting polymer being settled and collected, the collected polymer being dissolved in methalethylketone and settled again in hexane, and the settled material being fltered and dried in a vacuum. A white powdery polymer was obtained. The number mean molecular weight of the obtained polymer was 25,000 and its acid value was 75. In addition, it was confirmed from the existence of an absorption having a peak at 300 nm in the UV absorption spectrum of this polymer that GMA was copolymerized with NPG.

Workup

  1. additionwas added dropwise for 20 minutes
  2. stirringby stirring for further 2 hours
  3. filtrationby filtering
  4. customdrying the resulting crystals

Sources & evidence

ORD record
ord-48703719d8b14b51a4c236fac1b2c0fa
Source dataset
uspto-grants-1993_07
Patent number
US05227279

Reaction notes

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