3-(5-Nitrofuran-2-yl)prop-2-enal → 5-Nitro-2-[(o-butylbenzoylhydrazono)propen-1-yl]furan

HRID 2072400Notes

Reaction equation

HRID 2072400 reaction equation
[CH2:1]([C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([NH:9][NH2:10])=[O:8])[CH2:2][CH2:3][CH3:4].[N+:15]([C:18]1[O:22][C:21]([CH:23]=[CH:24][CH:25]=O)=[CH:20][CH:19]=1)([O-:17])=[O:16]>ClCCl>[N+:15]([C:18]1[O:22][C:21]([CH:23]=[CH:24][CH:25]=[N:10][NH:9][C:7](=[O:8])[C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 158633-(5-Nitrofuran-2-yl)prop-2-enalHCID 13157627Butyl benzhydrazide2×

Product 1

HCID 1515725-Nitro-2-[(o-butylbenzoylhydrazono)propen-1-yl]furan

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.7 g of the butyl benzhydrazide mentioned under (4) above in 20 ml of dichloromethane is mixed with a solution of 3.5 g of 3-(5-nitro-2-furyl)acrylaldehyde in 20 ml of dichloromethane, and the mixture is stirred at room temperature. The yellow-brown product (precipitated after a reaction time of 3 hours) is sucked off, the filtrate is concentrated, and the resulting solid material is likewise isolated. The two precipitates are recrystallized together from 200 ml of ethanol.

Workup

  1. customThe yellow-brown product (precipitated after a reaction time of 3 hours)
  2. concentrationthe filtrate is concentrated
  3. customthe resulting solid material is likewise isolated
  4. customThe two precipitates
  5. customare recrystallized together from 200 ml of ethanol

Sources & evidence

ORD record
ord-162d43a5ac5543a8a6376e8feb8bc634
Source dataset
uspto-grants-1977_09
Patent number
US04051253

Reaction notes

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