Chloroacetic Acid → N-(3,4-dichlorophenyl)glycine

HRID 28176Notes

Reaction equation

HRID 28176 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[C:10]([O-:13])(=[O:12])[CH3:11].[Na+].ClCC(O)=O.C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH:5][CH2:11][C:10]([OH:13])=[O:12]

Participants

8

Reactant 5

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 72573,4-DichloroanilineHCID 10340Sodium CarbonateHCID 517045Sodium Acetate

Product 1

HCID 351250N-(3,4-dichlorophenyl)glycineYield 62%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 32.4 g (0.2 mol) of 3,4-dichloroaniline and 28 g (0.2 mol) of sodium acetate in 200 ml of acetic acid and 40 ml of water is stirred under reflux. A solution of 28.5 g (0.3 mol) of chloroacetic acid and 15.9 g (0.15 mol) of sodium carbonate in 100 ml of water is run in over the course of half an hour. The mixture is kept under reflux for 3 hours, 30 ml of concentrated hydrochloric acid are added and the acetic acid is evaporated in vacuo. The residue is taken up in ether, the solution is washed with water and the acid is extracted with dilute sodium bicarbonate, reprecipitated with 3 N HCl, filtered off and dried. 27.2 g (62% yield) of acid, melting at 128°-130° C., are obtained.

Workup

  1. temperatureunder reflux
  2. customis run in over the course of half an hour
  3. temperatureunder reflux for 3 hours
  4. customthe acetic acid is evaporated in vacuo
  5. washthe solution is washed with water
  6. extractionthe acid is extracted with dilute sodium bicarbonate
  7. customreprecipitated with 3 N HCl
  8. filtrationfiltered off
  9. customdried

Sources & evidence

ORD record
ord-85cbb9b0c20a4cd5a18801efe44e7ed4
Source dataset
uspto-grants-1980_09
Patent number
US04225617

Reaction notes

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