M-Phenylenediamine → HCID 14699282, compound

HRID 1165879Notes

Reaction equation

HRID 1165879 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[CH3:9][O:10][CH2:11][C:12](Cl)=[O:13]>N1C=CC=CC=1>[CH3:9][O:10][CH2:11][C:12]([NH:7][C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([NH:8][C:12](=[O:13])[CH2:11][O:10][CH3:9])[CH:2]=1)=[O:13]

Participants

4

Reactant 2

HCID 7935M-PhenylenediamineHCID 96623Methoxyacetyl chloride

Product 1

HCID 14699282HCID 14699282, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of m-phenylenediamine (5.41 g) in pyridine (100 ml) is added dropwise methoxyacetyl chloride (10 ml). The mixture is stirred at room temperature for 2 hours, and thereafter, pyridine is distilled off under reduced pressure. To the residue is added water, and the mixture is extracted with chloroform. The organic layer is dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The resulting crude crystals are recrystallized from ethyl acetate-hexane to give the title compound (9.89 g) having the following physical properties.

Workup

  1. distillationpyridine is distilled off under reduced pressure
  2. additionTo the residue is added water
  3. extractionthe mixture is extracted with chloroform
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe resulting crude crystals are recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2ae9102334ca417f970562bd6d0c5a10
Source dataset
uspto-grants-1990_03
Patent number
US04912135

Reaction notes

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