2,4-Dichlorobenzoic Acid → 2,5-bis(2,4-dichlorophenyl)-1,3,4-oxadiazole

HRID 2058199Notes

Reaction equation

HRID 2058199 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8]>O>[Cl:4][C:5]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:6]=1[C:7]1[O:8][C:7]([C:6]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:5]=2[Cl:4])=[N:2][N:3]=1

Participants

4

Reactant 2

HCID 57872,4-Dichlorobenzoic AcidHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 2598372,5-bis(2,4-dichlorophenyl)-1,3,4-oxadiazoleYield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture was prepared by slowly adding 10 grams (g) of hydrazine hydrate to 400 g of vigorously stirring polyphosphoric acid at ~50° C. To this mixture was added 76 g (0.4 mole) of 2,4-dichlorobenzoic acid. A slurry developed and it was stirred at 125° C (+5°) for 5 hours. The reaction products were cooled slightly and poured into ~1.5 liter (1) of cold water. The solid which precipitated was recovered by filtration, washed with water, dried and recrystallized from chlorobenzene to give 54 g (75% of theoretical) of the desired 2,5-bis(2,4-dichlorophenyl)-1,3,4-oxadiazole.

Workup

  1. customA mixture was prepared
  2. temperatureThe reaction products were cooled slightly
  3. customThe solid which precipitated
  4. filtrationwas recovered by filtration
  5. washwashed with water
  6. customdried
  7. customrecrystallized from chlorobenzene

Sources & evidence

ORD record
ord-b7607cdee59d40dab50636d8ff8d0ea5
Source dataset
uspto-grants-1980_07
Patent number
US04215129

Reaction notes

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