Water → HCID 9840067, compound

HRID 726729Notes

Reaction equation

HRID 726729 reaction equation
[N+:1]([C:4]1[S:5][C:6]([CH:9]=O)=[CH:7][CH:8]=1)([O-:3])=[O:2].[C:11]1([S:17]([CH2:20][C:21]#[N:22])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C(O)C>[N+:1]([C:4]1[S:5][C:6](/[CH:9]=[C:20](/[S:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:18])=[O:19])\[C:21]#[N:22])=[CH:7][CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 782815-Nitrothiophene-2-carboxaldehydeHCID 82077Phenylsulphonylacetonitrile

Product 1

HCID 9840067HCID 9840067, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Nitrothiophen-5-carboxaldehyde (0.157 g) and phenylsulfonyl acetonitrile (0.199 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 0.16 g of (E)-3-(2-nitrothien-5-yl)-2-(phenylsulfonyl)acrylonitrile. Alternatively, the crude product was purified on a silica gel column with a mixture of ethylacetate and hexane as eluent.

Workup

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

Sources & evidence

ORD record
ord-d0081babd71247709971ddd4f0cc51b9
Source dataset
uspto-grants-1998_01
Patent number
US05710173

Reaction notes

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