Chloroacetic Acid → N-(4-Cyanophenyl)glycine

HRID 2394222Notes

Reaction equation

HRID 2394222 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)#[N:2].O.Cl[CH2:12][C:13]([OH:15])=[O:14]>C(OCC)(=O)C>[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH:7][CH2:12][C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 962Water2×HCID 133964-Aminobenzonitrile

Product 1

HCID 817965N-(4-Cyanophenyl)glycine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In a 500-ml three-necked flask, 4-cyanoaniline (100 g, 847.4 mmoles) was placed, followed by addition of 300 ml of water and attachment of a water cooling pipe, a mechanical stirrer and a dropping funnel. The flask was heated on an oil bath heated at 100° C. To the flask, an aqueous solution (water 150 ml) of monochloroacetic acid (104 g, 1116 mmoles) was added dropwise for about 30 minutes, followed by reflux with heating for 2.5 hours. After cooling naturally, about 100 ml of ethyl acetate was added to the flask to dissolve an insoluble matter. An organic layer was separated by a separatory funnel. The residual water layer and an aqueous layer obtained by extracting the organic layer with 100 ml of 5% (by weight) NaOH solution were combined, followed by acidolysis with 1/10N HCl. A precipitate produced was filtered and washed with water several times. After drying in an oven heated at 60° C. for 3 hours, the dried precipitate was dried in a vacuum desiccator overnight. The resulting product was a beige powder which showed no melting point but decomposed at 233.1° C. The yield was 38.8 g (26%).

Workup

  1. temperatureThe flask was heated on an oil bath
  2. temperatureby reflux
  3. temperaturewith heating for 2.5 hours
  4. temperatureAfter cooling naturally
  5. dissolutionto dissolve an insoluble matter
  6. customAn organic layer was separated by a separatory funnel
  7. customThe residual water layer and an aqueous layer obtained
  8. extractionby extracting the organic layer with 100 ml of 5% (by weight) NaOH solution
  9. customA precipitate produced
  10. filtrationwas filtered
  11. washwashed with water several times
  12. customAfter drying in an oven
  13. temperatureheated at 60° C. for 3 hours
  14. customthe dried precipitate was dried in a vacuum desiccator overnight
  15. customdecomposed at 233.1° C

Sources & evidence

ORD record
ord-d254e142905d4b408b8c6ef9b016807b
Source dataset
uspto-grants-1998_09
Patent number
US05811218

Reaction notes

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