Trimethylsilyl cyanide → N-(5-Cyano-7,8-dihydro-naphthalen-2-yl)-bezenesulfonamide

HRID 492083Notes

Reaction equation

HRID 492083 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:5]=[CH:4][C:3]1=2.C[Si]([C:26]#[N:27])(C)C>[I-].[Zn+2].[I-].CCOCC>[C:26]([C:2]1[C:3]2[CH:4]=[CH:5][C:6]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])=[CH:7][C:8]=2[CH2:9][CH2:10][CH:11]=1)#[N:27]

Participants

5

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 68830588N-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)benzenesulfonamide

Product 1

HCID 68860329N-(5-Cyano-7,8-dihydro-naphthalen-2-yl)-bezenesulfonamideYield 44%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 3283Diethyl EtherSolvent

Procedure

N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide (4.21 g, 14 mmol), trimethylsilyl cyanide (10.0 g, 100 mmol) and Zinc Iodide (0.25 g) were combined and stirred under nitrogen for 15 hours. The reaction mixture was then diluted by addition of 200 mL of Et2O, washed with cold water, and the organic layer was dried (MgSO4) and evaporated under reduced pressure to an oil. The oil was dissolved in 250 mL of toluene, and 0.5 g of paratoluene sulfonic acid was added. The reaction mixture was refluxed for three hours, cooled, and the the solvent was removed under reduced pressure. The crude product was eluted through silica under medium pressure with 5% EtOAc in hexanes to yield 1.89 g (6.1 mmol, 44%) of N-(5-Cyano-7,8-dihydro-naphthalen-2-yl)-bezenesulfonamide as an oil. MS: 311 (M+H)+.

Workup

  1. washwashed with cold water
  2. dry with materialthe organic layer was dried (MgSO4)
  3. customevaporated under reduced pressure to an oil
  4. dissolutionThe oil was dissolved in 250 mL of toluene
  5. addition0.5 g of paratoluene sulfonic acid was added
  6. temperatureThe reaction mixture was refluxed for three hours
  7. temperaturecooled
  8. customthe the solvent was removed under reduced pressure
  9. washThe crude product was eluted through silica under medium pressure with 5% EtOAc in hexanes

Sources & evidence

ORD record
ord-bf319e5c517e4484b54eac9026382186
Source dataset
uspto-grants-2009_05
Patent number
US07531577B2

Reaction notes

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