Chloroacetic Acid → 2-(Benzylamino)acetic acid

HRID 1709358Notes

Reaction equation

HRID 1709358 reaction equation
[Na].[C:2]([NH:10]O)(=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:13][C:14]([OH:16])=[O:15].Cl>C(O)C.O>[CH2:2]([NH:10][CH2:13][C:14]([OH:16])=[O:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 10313Benzohydroxamic acidHCID 5360545Sodium

Product 1

HCID 869652-(Benzylamino)acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Procedure

9.2 Grams (0.4 moles) of metallic sodium was dissolved in 300 ml of absolute ethanol. To the resulting solution, a solution of 27 g (0.2 moles) of benzhydroxamic acid in 600 ml of absolute ethanol was added dropwise 20°-25° C. with stirring for 3 hours. Subsequently, a solution of 9.5 g (0.1 mole) of chloroacetic acid in 100 ml of absolute ethanol was added dropwise and the resulting mixture wa stirred at 50° C. for 8 hours. After cooling the mixture, water was added and the mixture was neutralized with concentrated HCl. Ethanol was distilled off under vacuum and the pH of the residue was adjusted to 1 by addition of concentrated HCl. The precipitating crystal was recovered by filtration and dried to obtain benzamidooxyacetic acid in an amount of 8.2 g (yield, 42 mol %).

Workup

  1. stirringthe resulting mixture wa stirred at 50° C. for 8 hours
  2. additionwas added
  3. distillationEthanol was distilled off under vacuum
  4. additionthe pH of the residue was adjusted to 1 by addition of concentrated HCl
  5. filtrationThe precipitating crystal was recovered by filtration
  6. customdried

Sources & evidence

ORD record
ord-d1d06eef6dc24efc81fe08ca8e344a1f
Source dataset
uspto-grants-1990_08
Patent number
US04948916

Reaction notes

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