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

HRID 2255674Notes

Reaction equation

HRID 2255674 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[N+:7]([C:10]([N+:32]([O-:34])=[O:33])([N+:29]([O-:31])=[O:30])[CH2:11][CH2:12][C:13]([NH:15][NH:16][C:17](=[O:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])=O)([O-:9])=[O:8]>ClC(Cl)C>[N+:32]([C:10]([N+:7]([O-:9])=[O:8])([N+:29]([O-:31])=[O:30])[CH2:11][CH2:12][C:13]1[O:28][C:17]([C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])=[N:16][N:15]=1)([O-:34])=[O:33]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 19738486N-(4,4,4-trinitrobutyryl)-N'-(perfluorobutyryl)hydrazine

Product 1

HCID 197384752-(3,3,3-Trinitropropyl)-5-(perfluoropropyl)-1,3,4-oxadiazoleYield 66.9%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Phosphorus pentachloride (1.2 g, 0.0057 mole) and N-(4,4,4-trinitrobutyryl)-N'-(perfluorobutyryl)hydrazine (0.8 g, 0.0018 mole) in 10mL of dichloroethane was held at reflux temperature for 4 hours. Removal of volatiles 9ave an oil which was washed with water and then chromatographed on Silica gel 40 (CH2Cl2 as eluent) to give 0.5 g (66%) of 2-(3,3,3-trinitropropyl)-5-(perfluoropropyl)-1,3,4-oxadiazole, mp 43°-45° C.; 1H NMR (acetone): 3.84 (m, 2H), 4.23 (m, 2H). Anal. Calcd for C8H4F7N5O7 : C, 23.14; H, 0.97; F, 32.04; N, 16.87. Found: C, 23.07; H, 1.00; F, 31.80; N, 16.95.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. customRemoval of volatiles 9ave an oil which
  3. washwas washed with water
  4. customchromatographed on Silica gel 40 (CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-9764509ca39b47bbb1fb952422a15c02
Source dataset
uspto-grants-1993_08
Patent number
US05241071

Reaction notes

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