Ammonium Chloride → 4-Methylcarbamoylmethyl-o-phenylenediamine

HRID 35590Notes

Reaction equation

HRID 35590 reaction equation
[Cl-].[NH4+].[CH3:3][NH:4][C:5]([CH2:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[C:10]([N+:15]([O-])=O)[CH:9]=1)=[O:6]>O>[CH3:3][NH:4][C:5]([CH2:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[C:10]([NH2:15])[CH:9]=1)=[O:6]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 212945724-Methylcarbamoylmethyl-2-nitroaniline

Product 1

HCID 572720444-Methylcarbamoylmethyl-o-phenylenediamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reduced iron powder (9.87 g) and then a solution of ammonium chloride (0.373 g) in water (37 ml) were added to a solution of 4-methylcarbamoylmethyl-2-nitroaniline prepared as described in Example 8 (3.34 g) in industrial methylated spirit (186 ml). The mixture was heated under reflux for one hour and was then filtered through diatomaceous earth (sold under the trade name CELITE). The solid material collected was washed with hot industrial methylated spirit. The solvent was removed by evaporation an the residue dried by azeotropic distillation with toluene. The dried residue was recrystallised from industrial methylated spirit to give 4-methylcarbamoylmethyl-o-phenylenediamine (m.p. 140°-142° C.).

Workup

  1. customprepared
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for one hour
  4. filtrationwas then filtered through diatomaceous earth (
  5. customThe solid material collected
  6. washwas washed with hot industrial methylated spirit
  7. customThe solvent was removed by evaporation an the residue
  8. dry with materialdried by azeotropic distillation with toluene
  9. customThe dried residue was recrystallised from industrial methylated spirit

Sources & evidence

ORD record
ord-60acb857c07640548ae8543031ea077f
Source dataset
uspto-grants-1988_08
Patent number
US04767769

Reaction notes

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