Hydrochloric Acid → 1,4-Benzenedicarboxamide, N1,N4-dichloro-

HRID 1658599Notes

Reaction equation

HRID 1658599 reaction equation
[C:1]([NH2:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[ClH:13].[Cl:14]Cl>O>[Cl:13][NH:12][C:1](=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:8][Cl:14])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24526ChlorineHCID 76381Terephthalamide

Product 1

HCID 1086121,4-Benzenedicarboxamide, N1,N4-dichloro-Yield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

16.4 grams (0.10 mols) of terephthalamide were suspended in 500 ml. of a 17% by weight hydrochloric acid solution and heated in an enamel autoclave at 34°C. Then, by means of a dosing bulb and under intensive mixing, 22.8 grams (0.32 mols) of liquid chlorine was introduced into the autoclave. With water cooling, the reaction temperature was maintained at about 35°C. The reaction pressure amounted to 10 atm. After 5 minutes, the reaction from the autoclave, filtered and the residue washed with 200 ml. of water. The residue was then dried under vacuum at 70°C. There resulted 22.6 grams (97% of theory) of N,N'-dichloro-terephthalamide.

Workup

  1. customThe reaction pressure
  2. customthe reaction from the autoclave
  3. filtrationfiltered
  4. washthe residue washed with 200 ml
  5. customThe residue was then dried under vacuum at 70°C

Sources & evidence

ORD record
ord-f7851f047e124967a4d2f2ea7ef7b0e1
Source dataset
uspto-grants-1976_06
Patent number
US03965172

Reaction notes

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