Hydrochloric Acid → N-Methacryloyl glycine

HRID 978176Notes

Reaction equation

HRID 978176 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[C:8](Cl)(=[O:12])[C:9]([CH3:11])=[CH2:10].Cl>O>[C:8]([NH:1][CH2:2][C:3]([OH:5])=[O:4])(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

6

Reactant 4

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

Product 1

HCID 152645N-Methacryloyl glycineYield 48.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Glycine (75 g, 1 mol) is dissolved in 500 ml of 40 g (1 mol) of sodium hydroxide in the ice bath and the clear solution is reacted with 105 g (1 mol) of methacryloyl chloride and 40 g (1 mol) of sodium hydroxide in 150 ml of water simultaneously. The reaction temperature is kept below 5° C. throughout the addition. The reaction mixture is allowed to rise to room temperature and stirred at that temperature for three hours. The clear solution was titrated with 1N HCl to pH 3.0 and extracted with ethylacetate. The combined organic layer is dried over anhydrous magnesium sulfate and evaporated to leave 70 g (46%) of a crystalline material. Melting point 104° C. (literature 104°-105.5° C.). NMR (D2O), 5.7 gamma (s, 1H, =CH2), 5.4 gamma (s, 1H, =CH2), 4.0 gamma (s, 2H, CH2 ), 1.9 gamma (s, 3H, CH3). Purity by neutralization, 100.1%; purity by bromination, 100.8%.

Workup

  1. additionThe reaction temperature is kept below 5° C. throughout the addition
  2. customto rise to room temperature
  3. extractionextracted with ethylacetate
  4. dry with materialThe combined organic layer is dried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-a68892b6d2754a599ad63ded24a382fa
Source dataset
uspto-grants-1987_05
Patent number
US04663409

Reaction notes

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