Water → (E)-3-(2-nitrothien-5-yl)-2-[(pyridin-2-yl)sulfonyl]acrylonitrile

HRID 1419531Notes

Reaction equation

HRID 1419531 reaction equation
[N+:1]([C:4]1[S:5][C:6]([CH:9]=O)=[CH:7][CH:8]=1)([O-:3])=[O:2].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([CH2:20][C:21]#[N:22])(=[O:19])=[O:18].O>C(O)C>[N+:1]([C:4]1[S:5][C:6](/[CH:9]=[C:20](/[S:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)(=[O:19])=[O:18])\[C:21]#[N:22])=[CH:7][CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 782815-Nitrothiophene-2-carboxaldehydeHCID 5193552-Pyridinesulfonylacetonitrile

Product 1

HCID 15410661(E)-3-(2-nitrothien-5-yl)-2-[(pyridin-2-yl)sulfonyl]acrylonitrileYield 46.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Nitrothiophen-5-carboxaldehyde (0.157 g) and 2-pyridinesulphonylacetonitrile (0.2 g) were stirred in 2 mL of ethanol containing 0.01 mL piperidine for four hours at 100° C. The mixture was cooled to room temperature and water was added for crystalization. The crude product was filtered and recrystalized from ethanol and water to give 0.15 g of (E)-3-(2-nitrothien-5-yl)-2-[(pyridin-2-yl)sulfonyl] acrylonitrile.

Workup

  1. filtrationThe crude product was filtered
  2. customrecrystalized from ethanol and water

Sources & evidence

ORD record
ord-aaae46cd41f248e7ad73cc29d43850f3
Source dataset
uspto-grants-1999_03
Patent number
US05886195

Reaction notes

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