Water → HCID 23130496, compound

HRID 2080068Notes

Reaction equation

HRID 2080068 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.CCCCCC>[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

8

Reactant 4

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

Product 1

HCID 23130496HCID 23130496, compoundYield 72.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

5-Nitro-thiophene-2-carbonitrile(1.5 g, 9.7 mmol), phenol (1.8 g, 19.4 mmol) and potassium carbonate(4.0 g, 29.1 mmol) were suspended in dimethylsulfoxide (20 mL), and the mixture was stirred for 50 minutes at 60° C., followed by further stirring overnight at room temperature. Water and ethyl acetate were added to the reaction mixture, which was then partitioned, the organic layer was washed 4 times with water, then, 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, then hexane:ethyl acetate=20:1, then 10:1), and the title compound (1.4 g, 7.0 mmol, 72.1%) was obtained as a pale yellow oil.

Workup

  1. stirringby further stirring overnight at room temperature
  2. customwas then partitioned
  3. washthe organic layer was washed 4 times with water
  4. additionNH silica gel was added to the organic layer
  5. customthe solvent was evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record
ord-33bcbbf33ecb4d0bbad657ee50f66f17
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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