Sodium Hydroxide → 2-Chloro-p-Phenylenediamine

HRID 2082651Notes

Reaction equation

HRID 2082651 reaction equation
S(O)(O)(=O)=O.[Cl:6][C:7]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:8]=1[NH2:14].[OH-].[Na+]>O>[Cl:6][C:7]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:8]=1[NH2:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 225842-Chloro-p-phenylenediamine sulfate

Product 1

HCID 119982-Chloro-p-Phenylenediamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-1,4-phenylenediamine sulfate, ##STR9## was dissolved in water, neutralized with an aqueous sodium hydroxide solution, and extracted with ethyl ether. The ether extract layer, after removal of the ether, was purified by recrystallization, repeated twice, from chlorobenzene, and dried to obtain 2-chloro-1,4-phenylenediamine, ##STR10## In 500 ml of benzene, were dissolved 0.1 mole of said 2-chloro-1,4-phenylenediamine and 0.2 mole of distilled and dried p-methylbenzaldehyde. The resulting solution was refluxed for about 4 hours, while removing the azeotropically distilled water by means of a Dean-Stark trap. Thereafter, the solvent was removed from the reaction mixture by distillation by use of a rotary evaporator. The distillation residue was collected and purified by repeated recrystallization from isopropyl alcohol until a constant melting point was attained to obtain bis(4'-methylbenzal)-2-chloro-1,4-phenylenediamine, ##STR11## (Compound H), which showed M.R. of 144.4° - 196.6° C.

Workup

  1. extractionextracted with ethyl ether
  2. extractionThe ether extract layer
  3. customafter removal of the ether
  4. customwas purified by recrystallization
  5. customdried

Sources & evidence

ORD record
ord-59ba8f8ee0984b8cb746c7eadfa0ebf9
Source dataset
uspto-grants-1978_04
Patent number
US04082686

Reaction notes

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