Hydrochloric Acid → N-Methacryloyl glycine

HRID 1581889Notes

Reaction equation

HRID 1581889 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>C(Cl)(Cl)Cl>[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 Hydroxide

Product 1

HCID 152645N-Methacryloyl glycine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Glycine (7.5 g, 0.1 moles) is dissolved in 30 ml of aqueous sodium hydroxide solution (8 g, 0.2 moles) and cooled in ice and methacryloyl chloride (10.45 g, 0.1 moles), dissolved in 10 ml of chloroform, is added dropwise with stirring. After that, the reaction is allowed to continue for one hour at room temperature. The solution, cooled in ice, is acidified to a pH of 2 with 5N aqueous hydrochloric acid and exhaustively extracted with ethyl acetate. The organic solution is dried over sodium sulfate and evaporated under vacuum, 10 g (70%) of a crystalline product of N-methyacryloyl glycine with a melting point of 104° C. to 105° C. being obtained.

Workup

  1. temperaturecooled in ice
  2. additionis added dropwise
  3. temperatureThe solution, cooled in ice
  4. extractionexhaustively extracted with ethyl acetate
  5. dry with materialThe organic solution is dried over sodium sulfate
  6. customevaporated under vacuum, 10 g (70%) of a crystalline product of N-methyacryloyl glycine with a melting point of 104° C. to 105° C.
  7. custombeing obtained

Sources & evidence

ORD record
ord-2070dc82ee2f4f4bb533ac26bef974c8
Source dataset
uspto-grants-2004_05
Patent number
US06733123B2

Reaction notes

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