Hydrochloric Acid → N-(4,4,4-trinitrobutyryl)-N'-(perfluorobutyryl)hydrazine

HRID 2255673Notes

Reaction equation

HRID 2255673 reaction equation
[N+:1]([C:4]([N+:13]([O-:15])=[O:14])([N+:10]([O-:12])=[O:11])[CH2:5][CH2:6][C:7](Cl)=[O:8])([O-:3])=[O:2].[F:16][C:17]([F:29])([C:25]([F:28])([F:27])[F:26])[C:18]([F:24])([F:23])[C:19]([NH:21][NH2:22])=[O:20].N1C=CC=CC=1.Cl>C(OCC)C.O>[N+:1]([C:4]([N+:13]([O-:15])=[O:14])([N+:10]([O-:12])=[O:11])[CH2:5][CH2:6][C:7]([NH:22][NH:21][C:19](=[O:20])[C:18]([F:23])([F:24])[C:17]([F:16])([F:29])[C:25]([F:27])([F:26])[F:28])=[O:8])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 2467902,2,3,3,4,4,4-HeptafluorobutanehydrazideHCID 125075564,4,4-Trinitrobutyryl chloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 1.0 g (0.0041 mole) of 4,4,4-trinitrobutyryl chloride in anhydrous diethyl ether (10 mL) stirred at 20° C. (water bath) was added 0.9 g (0.0039 mole) of N-(heptafluorobutyryl)hydrazine. The mixture became thick with precipitate and sufficient ether (10 mL) was added to allow efficient stirring. Pyridine (0.35 ml, 0.0044 mole) was added dropwise and the mixture was stirred for 5 minutes before 5% hydrochloric acid (10 mL) was added. The ether layer was dried (Na2SO4), the volatiles were removed, and the residue was stirred with water to give 1.5 g, mp 146°-150° C. Crystallization from 1,2-dichloroethane gave the product, N-(4,4,4-trinitrobutyryl)-N'-(perfluorobutyryl)hydrazine, 1.2 g (70%) mp 154°-156° C.; 1H NMR (acetone-d6 +D2O): 2.98 (t, 2H), 3.87 (t, 2H).

Workup

  1. additionwas added
  2. additionwas added
  3. dry with materialThe ether layer was dried (Na2SO4)
  4. customthe volatiles were removed
  5. customto give 1.5 g, mp 146°-150° C
  6. customCrystallization from 1,2-dichloroethane

Sources & evidence

ORD record
ord-5713548f3a114501a9236327274a1db9
Source dataset
uspto-grants-1993_08
Patent number
US05241071

Reaction notes

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