Sodium Chloride → 67749-20-6

HRID 866309Notes

Reaction equation

HRID 866309 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:21][C:22]([Cl:27])([Cl:26])[C:23](Cl)=[O:24].[Cl-].[Na+]>C1C=CC=CC=1>[NH:7]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:23](=[O:24])[C:22]([Cl:27])([Cl:26])[Cl:21])=[CH:10][CH:9]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6420Trichloroacetyl chlorideHCID 7564N-Phenyl-p-phenylenediamineHCID 10340Sodium Carbonate

Product 1

HCID 75910767749-20-6

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The following materials are charged to a reactor: 62.5 g (0.34 mole) 4-aminodiphenylamine, 39 g (0.37 mole) sodium carbonate and 500 ml benzene. To this stirred mixture, under nitrogen, is added a solution of 63.8 (0.35 mole) trichloroacetyl chloride in 100 ml benzene over a thirty minute period. Stirring is continued for another 31/2 hours. The crude product containing sodium chloride by-product is dried to remove solvent. The dried material is washed first with dilute HCl, then distilled water, air dried and the product is recrystallized from a methanol/benzene (1/2) solvent mixture. Melting point and elementary analysis are reported in Table I.

Workup

  1. additionThe following materials are charged to a reactor
  2. custom2 hours
  3. customis dried
  4. customto remove solvent
  5. washThe dried material is washed first with dilute HCl
  6. dry with materialdistilled water, air dried
  7. customthe product is recrystallized from a methanol/benzene (1/2) solvent mixture

Sources & evidence

ORD record
ord-65e692e222484066a965cf7beefd7e7c
Source dataset
uspto-grants-1978_07
Patent number
US04098760

Reaction notes

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