Phosphorus pentachloride → 2-(3,3,3-Trinitropropyl)-5-(perfluoroethyl)-1,3,4-oxadiazole

HRID 2255676Notes

Reaction equation

HRID 2255676 reaction equation
[N+:1]([C:4]([N+:23]([O-:25])=[O:24])([N+:20]([O-:22])=[O:21])[CH2:5][CH2:6][C:7]([NH:9][NH:10][C:11](=[O:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])=O)([O-:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)Cl>ClCCCl.C(Cl)Cl>[N+:1]([C:4]([N+:23]([O-:25])=[O:24])([N+:20]([O-:22])=[O:21])[CH2:5][CH2:6][C:7]1[O:19][C:11]([C:12]([F:17])([F:18])[C:13]([F:15])([F:16])[F:14])=[N:10][N:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 19738489N-(4,4,4-trinitrobutyryl)-N'-(perfluoropropionyl)hydrazine

Product 1

HCID 197384882-(3,3,3-Trinitropropyl)-5-(perfluoroethyl)-1,3,4-oxadiazole

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution containing 0.6 g (0.0016 mole) of N-(4,4,4-trinitrobutyryl)-N'-(perfluoropropionyl)hydrazine and 0.8 g (0.0038 mole) of phosphorus pentachloride in 7 mL of 1,2-dichloroethane was held at reflux temperature for 4 hours before the volatiles were removed to give an oil residue. The residue was dissolved in CH2Cl2, washed with water, and chromatographed on Silica gel 40 (CH2Cl2 as eluent) to give the product, 2-(3,3,3-trinitropropyl)-5-(perfluoroethyl)-1,3,4-oxadiazole, 0.4 g (70%), mp 36°-38° C. 1H NMR (acetone-d6): 3.80 (m, 2H), 4.20 (m, 2H).

Workup

  1. temperatureat reflux temperature for 4 hours before the volatiles
  2. customwere removed
  3. customto give an oil residue
  4. washwashed with water
  5. customchromatographed on Silica gel 40 (CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-7c9dda161f0b4d0cad2a94cf756e797d
Source dataset
uspto-grants-1993_08
Patent number
US05241071

Reaction notes

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