Chloroacetic Acid → HCID 178423949, compound

HRID 986668Notes

Reaction equation

HRID 986668 reaction equation
[CH3:1][C:2]1[C:3]([NH2:9])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[Cl:10][CH2:11][C:12](O)=O.[OH-].[NH4+]>Cl>[Cl:10][CH2:11][C:12]1[NH:9][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[N:8]=1

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 14923Ammonium HydroxideHCID 175932,3-Diaminotoluene

Product 1

HCID 178423949HCID 178423949, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1.83 g (15 m mol) of 3-methyl-1,2-phenylenediamine in 20 ml of 4N aqueous hydrochloric acid was stored at room temperature overnight. To the solution was added 2.13 g (22.5 m mol) of monochloroacetic acid and refluxed for 3 hours. The reaction solution was cooled to room temperature, rendered alkaline by addition of ammonium hydroxide and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried on anhydrous sodium sulfate. The solvent was evaporated in vacuo and the residue was crystallized from ethyl ether to give 0.8 g (29.52%).

Workup

  1. temperaturerefluxed for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was crystallized from ethyl ether
  7. customto give 0.8 g (29.52%)

Sources & evidence

ORD record
ord-5e6d84a89fcd44758b7499b5ab518283
Source dataset
uspto-grants-1987_12
Patent number
US04714764

Reaction notes

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