Water → HCID 9840067, compound

HRID 1419530Notes

Reaction equation

HRID 1419530 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 crystallization. The crude product was filtered and recrystallized 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. customrecrystallized from ethanol and water

Sources & evidence

ORD record
ord-e3ec7915bdc6469698be0a71c206294b
Source dataset
uspto-grants-1999_03
Patent number
US05886195

Reaction notes

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