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

HRID 2255678Notes

Reaction equation

HRID 2255678 reaction equation
[F:1][C:2]([N+:11]([O-:13])=[O:12])([N+:8]([O-:10])=[O:9])[CH2:3][CH2:4][C:5](Cl)=[O:6].[F:14][C:15]([F:24])([C:20]([F:23])([F:22])[F:21])[C:16]([NH:18][NH2:19])=[O:17].N1C=CC=CC=1.Cl>C(OCC)C>[F:1][C:2]([N+:11]([O-:13])=[O:12])([N+:8]([O-:10])=[O:9])[CH2:3][CH2:4][C:5]([NH:19][NH:18][C:16](=[O:17])[C:15]([F:14])([F:24])[C:20]([F:22])([F:23])[F:21])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 2467892,2,3,3,3-PentafluoropropanehydrazideHCID 125075584-Fluoro-4,4-dinitrobutyryl chloride

Product 1

HCID 19738478N-(4-fluoro-4,4-dinitrobutyryl)-N'-(perfluoropropionyl)hydrazine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 0.95 g (0.0045 mole) of 4-fluoro-4,4-dinitrobutyryl chloride in 20 mL of anhydrous diethyl ether stirred at 20° C. was added 0.8 g (0.0045 mole) of N-(perfluoropropionyl)hydrazine followed by the dropwise addition of 0.4 mL of pyridine. After 5 minutes, dilute hydrochloric acid (10 mL) was added, the ether layer was separated, dried (Na2SO4) and the volatiles were removed to give the product N-(4-fluoro-4,4-dinitrobutyryl)-N'-(perfluoropropionyl)hydrazine, 1.05 g, mp 128°-132° C. Crystallization from 1,2-dichloroethane gave 0.93 g (58%), mp 135°-136° C. 1H NMR (acetone d6 +D2O): 2.80 (t, 2H), 3.36, 3.58 (d of t, 2H).

Workup

  1. customthe ether layer was separated
  2. dry with materialdried (Na2SO4)
  3. customthe volatiles were removed

Sources & evidence

ORD record
ord-4aa5b2d729e4470aa430ae08eb792cf4
Source dataset
uspto-grants-1993_08
Patent number
US05241071

Reaction notes

Loading…