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

HRID 2255675Notes

Reaction equation

HRID 2255675 reaction equation
[F:1][C:2]([F:11])([C:7]([F:10])([F:9])[F:8])[C:3]([NH:5][NH2:6])=[O:4].[N+:12]([C:15]([N+:24]([O-:26])=[O:25])([N+:21]([O-:23])=[O:22])[CH2:16][CH2:17][C:18](Cl)=[O:19])([O-:14])=[O:13].Cl.C(=O)(O)[O-].[Na+]>C(OCC)C.N1C=CC=CC=1>[N+:12]([C:15]([N+:21]([O-:23])=[O:22])([N+:24]([O-:26])=[O:25])[CH2:16][CH2:17][C:18]([NH:6][NH:5][C:3](=[O:4])[C:2]([F:11])([F:1])[C:7]([F:8])([F:9])[F:10])=[O:19])([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2467892,2,3,3,3-PentafluoropropanehydrazideHCID 516892Sodium BicarbonateHCID 125075564,4,4-Trinitrobutyryl chloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture formed by adding 0.77 g (0.0043 mole) of N-(perfluoropropionyl)hydrazine to a solution of 1.05 g (0.0043 mole) of 4,4,4-trinitrobutyryl chloride in 30 mL of anhydrous diethyl ether was stirred at 20° C during the dropwise addition of 0.35 mL of pyridine. After 5 minutes, dilute hydrochloric acid (10 mL) was added, and the ether layer was separated and dried (MgSO4). Removal of volatiles gave a semisolid which was stirred with dilute sodium bicarbonate to give 1.0 g, mp 105°-118° C. Crystallization from 1,2-dichloroethane gave the product, N-(4,4,4-trinitrobutyryl)-N'-(perfluoropropionyl)hydrazine, 0.65 g (41%), mp 123°-125° C.; 1H NMR (acetone-d6 +D2O): 2.95 (t, 2H); 3.85 (t, 2H).

Workup

  1. customA mixture formed
  2. customthe ether layer was separated
  3. dry with materialdried (MgSO4)
  4. customRemoval of volatiles
  5. customgave a semisolid which
  6. customto give 1.0 g, mp 105°-118° C
  7. customCrystallization from 1,2-dichloroethane

Sources & evidence

ORD record
ord-ec8739fb6c0641a3bbda6a02ff51b17f
Source dataset
uspto-grants-1993_08
Patent number
US05241071

Reaction notes

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