1,2-Dichloroethane → HCID 12346245, compound

HRID 867956Notes

Reaction equation

HRID 867956 reaction equation
[N+:1]([C:4]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[C:27]([N+:34]([O-:36])=[O:35])[C:5]=1[C:6]([NH:8][NH:9][C:10](=[O:26])[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:14]([N+:20]([O-:22])=[O:21])=[CH:13][C:12]=1[N+:23]([O-:25])=[O:24])=O)([O-:3])=[O:2].ClCCCl.P(Cl)(Cl)(Cl)(Cl)Cl>CO>[C:5]1([C:6]2[O:26][C:10]([C:11]3[C:12]([N+:23]([O-:25])=[O:24])=[CH:13][C:14]([N+:20]([O-:22])=[O:21])=[CH:15][C:16]=3[N+:17]([O-:19])=[O:18])=[N:9][N:8]=2)[C:27]([N+:34]([O-:36])=[O:35])=[CH:28][C:29]([N+:31]([O-:33])=[O:32])=[CH:30][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 24819Phosphorus pentachlorideHCID 12346235HCID 12346235, compound

Product 1

HCID 12346245HCID 12346245, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 7.4 g (0.0145 mol) of N,N'-bis(2,4,6-trinitrobenzoyl)hydrazine and 65 ml of 1,2-dichloroethane stirred in a 200 ml round bottom flask was added 7.4 g (0.0355 mol) of phosphorus pentachloride. The mixture was heated to reflux temperature in an oil bath and was held at this temperature for 2.5 hrs. The mixture was cooled to room temperature and the insoluble material (3.2 g of crude 2,5-dipicryl-1,3,4-oxadiazole, mp 318° C. (dec), was removed by filtration. The crude oxadiazole was dissolved in boiling acetone (300 ml), the solution was filtered and the filtrate was concentrated by distillation until much of the acetone had been removed and an appreciable amount of crystals had formed. Methanol was slowly added with continued distillation until the distillate temperature approached 65° C. The mixture was cooled to room temperature and filtered to give 2.9 g of pure 2,5-dipicryl1,3,4-oxadiazole, mp 335° C. (vigorous decomposition). NMR (DMSO-d6):9.52 (s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux temperature in an oil bath
  3. customthe insoluble material (3.2 g of crude 2,5-dipicryl-1,3,4-oxadiazole, mp 318° C. (dec), was removed by filtration
  4. dissolutionThe crude oxadiazole was dissolved
  5. filtrationthe solution was filtered
  6. concentrationthe filtrate was concentrated by distillation until much of the acetone
  7. customhad been removed
  8. customan appreciable amount of crystals had formed
  9. customapproached 65° C
  10. temperatureThe mixture was cooled to room temperature
  11. filtrationfiltered

Sources & evidence

ORD record
ord-8591abc2eacb468aa35852dac1845343
Source dataset
uspto-grants-1988_10
Patent number
US04777258

Reaction notes

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