Hydrochloric Acid → Acetic acid, 2-((2-chlorobenzoyl)amino)-

HRID 44438Notes

Reaction equation

HRID 44438 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[Cl:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](Cl)=[O:12].Cl>O>[Cl:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 14798Sodium HydroxideHCID 691102-Chlorobenzoyl chloride

Product 1

HCID 177756Acetic acid, 2-((2-chlorobenzoyl)amino)-Yield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of glycine (100 mmol) and NaOH (100 mmol) in water (300 ml), at 5° C., o-chloro-benzoyl chloride (110 mmol) was added in small portions. The reaction mixture was stirred for 30 minutes at room temperature, then cooled again and acidified to pH=2 by addition of 6 M HCl. Extraction of the aqueous solution was performed with EtOAc. Then, the combined organic layers were dried over MgSO4 and the solvent was removed by reduced pressure. The residue was triturated in boiling chloroform, and the product was collected by filtration in 80% yield.

Workup

  1. temperaturecooled again
  2. extractionExtraction of the aqueous solution
  3. dry with materialThen, the combined organic layers were dried over MgSO4
  4. customthe solvent was removed by reduced pressure
  5. customThe residue was triturated
  6. filtrationthe product was collected by filtration in 80% yield

Sources & evidence

ORD record
ord-4a9fdad254f04dc1b4dd32db485b3fe6
Source dataset
uspto-grants-2013_09
Patent number
US08541428B2

Reaction notes

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