4-Aminobenzoic Acid → 4,4'-(1,3,4-Oxadiazole-2,5-diyl)dianiline

HRID 1249135Notes

Reaction equation

HRID 1249135 reaction equation
S(O)(O)(=O)=O.[NH2:6][NH2:7].[NH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1.[OH-].[Na+]>OS(O)(=O)=O.O=S(=O)=O>[NH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]2[O:14][C:13]([C:12]3[CH:16]=[CH:17][C:9]([NH2:8])=[CH:10][CH:11]=3)=[N:6][N:7]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 14798Sodium HydroxideHCID 24842Hydrazine Sulfate

Product 1

HCID 755054,4'-(1,3,4-Oxadiazole-2,5-diyl)dianilineYield 63.3%

Reagents, catalysts & solvents 1

HCID 24681Fuming sulfuric acidSolvent

Procedure

60 g (0.46 mole) of hydrazine sulphate was dissolved in 700 ml of oleum with 20% SO3. 137 g (1.0 mol) p-aminobenzoic acid was added at room temperature. The mixture was stirred for 2.5 hours at a temperature of 70° C. to 75° C. and then poured onto 10 liters of ice and neutralized with a concentrated sodium hydroxide solution. The resulting precipitate was filtered off, washed with water, and again filtered off. The yield was 91 g of impure product. This impure product was recrystallized in ethanol. After partial evaporation of the resulting liquid, 73.5 g of pure 2,5-bis-(p-aminophenyl)-1,3,4-oxadiazole were obtained.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with water
  3. filtrationagain filtered off
  4. customThis impure product was recrystallized in ethanol
  5. customAfter partial evaporation of the resulting liquid

Sources & evidence

ORD record
ord-02a48e60de8d4d45854d1cf2f15561b8
Source dataset
uspto-grants-1986_12
Patent number
US04629671

Reaction notes

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