Water → HCID 23130496, compound

HRID 2080067Notes

Reaction equation

HRID 2080067 reaction equation
[N+]([C:4]1[S:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=1)([O-])=O.[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(OCC)(=O)C>[O:17]([C:4]1[S:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium CarbonateHCID 5192945-Nitrothiophene-2-carbonitrile

Product 1

HCID 23130496HCID 23130496, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Nitrothiophene-2-carbonitrile (0.80 g, 5.2 mmol), phenol (1.0 g, 10.4 mmol) and potassium carbonate (2.2 g, 15.6 mmol) were suspended in dimethylsulfoxide (30 mL), and the mixture was stirred at room temperature for 15.5 hours. Water and ethyl acetate were added for partitioning, and the organic layer was washed three times with water. NH silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purification was carried out by NH silica gel column chromatography (hexane:ethyl acetate=8:1), and 5-phenoxythiophene-2-carbonitrile (720 mg, 3.6 mmol, 69.2%) was obtained as a colorless oil.

Workup

  1. customfor partitioning
  2. washthe organic layer was washed three times with water
  3. additionNH silica gel was added to the organic layer
  4. customthe solvent was evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record
ord-30279d2baadc4b719273b71364a77e78
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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