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

HRID 2255677Notes

Reaction equation

HRID 2255677 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:23])([F:22])[C:18]([NH:20][NH2:21])=[O:19].N1C=CC=CC=1.Cl>C(OCC)C>[N+:1]([C:4]([N+:13]([O-:15])=[O:14])([N+:10]([O-:12])=[O:11])[CH2:5][CH2:6][C:7]([NH:21][NH:20][C:18](=[O:19])[C:17]([F:23])([F:22])[F:16])=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 229753TrifluoroacetohydrazideHCID 125075564,4,4-Trinitrobutyryl chloride

Product 1

HCID 19738490N-(4,4,4-trinitrobutyryl)-N'-(trifluoroacetyl)hydrazine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 1.65 g (0.007 mole) of 4,4,4-trinitrobutyryl chloride in 15 mL of anhydrous diethyl ether stirred in a water bath at 15° C. was added 0.9 g (0.007 mole) of N-(trifluoroacetyl)hydrazine. Pyridine (0.6 mL, 0.007 mole) was added dropwise. After 3 minutes, dilute hydrochloric acid was added and the ether layer was separated and dried (Na2SO4). The volatiles were removed and the residue was stirred with water and then with CH2Cl2 to give the product N-(4,4,4-trinitrobutyryl)-N'-(trifluoroacetyl)hydrazine, 1.15 g (50%), mp 154°-156° C. Crystallization from 1,2-dichloroethane raised the melting point to 157°-159° C.; 1H NMR (acetone-d6 +D2O): 2.97 (t, 2H), 3.86 (t, 2H); IR (KBr): 3330, 3220 (NH), 1745, 1690 (C=O); 1610, 1590 (NO2); 1195 (C--F).

Workup

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

Sources & evidence

ORD record
ord-cd6378f167c343a8b51d4310fdf8df54
Source dataset
uspto-grants-1993_08
Patent number
US05241071

Reaction notes

Loading…