Potassium Hydroxide → HCID 23023846, compound

HRID 851873Notes

Reaction equation

HRID 851873 reaction equation
O1CCOCC1.[C:7]([C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[O:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)=[S:13])#[N:8].[OH-].[K+]>[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+].O>[C:7]([C:9]1[CH:10]=[C:11]([C:12]2[S:13][C:16]3[C:17]([O:21][CH3:22])=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=2)[CH:23]=[CH:24][C:25]=1[O:26][CH2:27][CH:28]([CH3:30])[CH3:29])#[N:8]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 23023848HCID 23023848, compound

Product 1

HCID 23023846HCID 23023846, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 178511488HCID 178511488, compoundCatalystHCID 962WaterSolvent

Procedure

Dioxane (70 mL) and water (70 mL) were added to a mixture of 3-cyano-4-isobutyloxy-N-(3-methoxyphenyl)thiobenzamide (900 mg, 2.64 mmol), potassium ferricyanide (2.61 g, 7.93 mmol), and potassium hydroxide (892 mg, 15.9 mmol). The resulting mixture was stirred for 20 hours at room temperature. The mixture was then placed under reduced pressure to distill the solvent off, and extracted with ethyl acetate (50 mL). The ethyl acetate portion was washed with water, dried over anhydrous magnesium sulfate, and placed under reduced pressure to distill the solvent off. The residue was purified by silica gel column chromatography (ethyl acetate/toluene=1/20-1/10), to give 322 mg (yield 36%) of the desired compound in the form of a pale yellow crystalline product.

Workup

  1. distillationto distill the solvent off, and
  2. extractionextracted with ethyl acetate (50 mL)
  3. washThe ethyl acetate portion was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationto distill the solvent off
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/toluene=1/20-1/10)

Sources & evidence

ORD record
ord-a2c66849b2e34f5d88ff9392f044cb39
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

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