Water → HCID 15405933, compound

HRID 1415737Notes

Reaction equation

HRID 1415737 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([N:7]=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C[Si]([C:25]#[N:26])(C)C.O>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:7][CH:8]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[C:25]#[N:26])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 962WaterHCID 82115Trimethylsilyl cyanideHCID 21862856HCID 21862856, compound

Product 1

HCID 15405933HCID 15405933, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.48 g (5.1 mmol) of 4-methoxy-N-(4-methylsulfonylbenzylidene)aniline [prepared as described in step (i) above] were suspended in 15 ml of anhydrous tetrahydrofuran, and 0.80 ml (6.0 mmol) of 95% trimethylsilyl cyanide and 0.85 g (6.0 mmol) of zinc chloride were added to the resulting suspension at 0° C., whilst stirring. The temperature of the reaction mixture was then allowed to return to room temperature, and the mixture was stirred overnight. At the end of this time, water was added and the mixture was extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous sodium sulfate, after which it was concentrated by evaporation under reduced pressure and the crystals which precipitated were collected by filtration, to give 1.05 g (yield 65%) of the title compound as a slightly yellow powder.

Workup

  1. customto return to room temperature
  2. stirringthe mixture was stirred overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationafter which it was concentrated by evaporation under reduced pressure
  8. customthe crystals which precipitated
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-f7025026e8214212b13892344801fff0
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

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