5-Nitrothiophene-2-carboxaldehyde → HCID 67582692, compound

HRID 726745Notes

Reaction equation

HRID 726745 reaction equation
[N+:1]([C:4]1[S:5][C:6]([CH:9]=O)=[CH:7][CH:8]=1)([O-:3])=[O:2].[S:11]([CH2:17][C:18]#[N:19])([CH2:14][C:15]#[N:16])(=[O:13])=[O:12]>C(O)C.N1CCCCC1>[C:15]([CH2:14][S:11](/[C:17](=[CH:9]/[C:6]1[S:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:8][CH:7]=1)/[C:18]#[N:19])(=[O:13])=[O:12])#[N:16].[C:15](/[C:14](/[S:11](/[C:17](=[CH:9]/[C:6]1[S:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:8][CH:7]=1)/[C:18]#[N:19])(=[O:13])=[O:12])=[CH:9]\[C:6]1[S:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:8][CH:7]=1)#[N:16]

Participants

6

Reactant 2

HCID 782815-Nitrothiophene-2-carboxaldehydeHCID 142163Sulphonyl diacetonitrile

Product 2

HCID 67582692HCID 67582692, compoundHCID 88414059HCID 88414059, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of (0.5 g) of 2-nitrothiophen-5-carboxaldehyde and (0.7 g) of sulfonyl diacetonitrile in 6 mL ethanol was refluxed with a few drops of piperidine for 4 hours. Ethanol was removed in a rotavap and the mixture worked up with ethylacetate, diluted acid and brine. A portion of the crude was then purified by HPLC on a C-18 column to provide (0.05 g) of (E)-2-cyanomethylsulfonyl-3-(2-nitrothien-5-yl)acrylonitrile along with (0.03 g) of (E,E)-2-[[1-cyano-2-(2-nitrothien-5-yl)ethenyl]sulfonyl]-3-(2-nitrothien-5-yl)acrylonitrile.

Workup

  1. customEthanol was removed in a rotavap
  2. additiondiluted acid and brine
  3. customA portion of the crude was then purified by HPLC on a C-18 column

Sources & evidence

ORD record
ord-3dcc6fd963ca4a3b83425bf6b2ba5022
Source dataset
uspto-grants-1998_01
Patent number
US05710173

Reaction notes

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