Hydrochloric Acid → N-Methacryloyl glycine

HRID 2413013Notes

Reaction equation

HRID 2413013 reaction equation
[OH-].[Na+].[N+](C1C=CC=CC=1)([O-])=O.[NH2:12][CH2:13][C:14]([OH:16])=[O:15].[C:17](Cl)(=[O:21])[C:18]([CH3:20])=[CH2:19].Cl>O.C(#N)C>[C:17]([NH:12][CH2:13][C:14]([OH:16])=[O:15])(=[O:21])[C:18]([CH3:20])=[CH2:19]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 750GlycineHCID 7416NitrobenzeneHCID 13528Methacryloyl chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 152645N-Methacryloyl glycineYield 40.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

In a mixture composed of 80 g (2.0 mols) of sodium hydroxide, 400 ml of water and 4 ml of nitrobenzene was dissolved with stirring 150 g (2.0 mols) of glycine and the resulting solution was cooled to 0° C. To the aqueous solution, there were simultaneously added dropwise 230 g (2.2 mols) of methacrylic chloride and an aqueous solution containing 96 g (2.4 mols) of sodium hydroxide dissolved in 200 ml of water. After the completion of the reaction, 800 ml of acetonitrile was added to the reaction solution and the mixture was then acidified by adding 160 ml of concentrated hydrochloric acid. 1 Liter of acetonitrile was further added to extract and the acetonitrile layer was separated. The acetonitrile solution was concentrated and the crystals thus deposited were collected and recrystallized from ethyl acetate to obtain 117 g of N-methacryloyl glycine.

Workup

  1. dissolutionwas dissolved
  2. additionwas added to the reaction solution
  3. extractionto extract
  4. customthe acetonitrile layer was separated
  5. concentrationThe acetonitrile solution was concentrated
  6. customthe crystals thus deposited were collected
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a663907452c0400593064d3f4418b2d9
Source dataset
uspto-grants-1985_01
Patent number
US04495272

Reaction notes

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