Water → HCID 23130625, compound

HRID 2080122Notes

Reaction equation

HRID 2080122 reaction equation
[N+]([C:4]1[S:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=1)([O-])=O.[Cl:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][C:4]1[S:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79333-ChlorophenolHCID 11430Potassium CarbonateHCID 5192945-Nitrothiophene-2-carbonitrile

Product 1

HCID 23130625HCID 23130625, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

5-Nitro-thiophene-2-carbonitrile (5.00 g, 32.5 mmol), 3-chloro-phenol (6.90 mL, 65.0 mmol) and potassium carbonate (13.4 g, 97.5 mmol) were suspended in dimethylsulfoxide (50 mL), and the mixture was stirred at 60° C. for 4 hours. Water was added to the reaction mixture at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with water twice, and further washed with brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel silica gel column chromatography (hexane:ethyl acetate=20:1), and the title compound (5.56 g, 23.6 mmol, 73%) was obtained as a pale yellow oil.

Workup

  1. extractionwhich was then extracted with ethyl acetate
  2. washthe organic layer was washed with water twice
  3. washfurther washed with brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by NH silica gel silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-d081c955f2b0410f9d2c22a1c742b180
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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