Trimethylsilyl cyanide → HCID 521386, compound

HRID 441064Notes

Reaction equation

HRID 441064 reaction equation
C[Si]([C:5]#[N:6])(C)C.[C:7](=[NH:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1C=CC=CC=1.[I-].[Zn+2].[I-]>[C:8]1([C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([NH2:20])[C:5]#[N:6])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 136809Benzophenone imine

Product 1

HCID 521386HCID 521386, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 241BenzeneSolvent

Procedure

A solution of 4.05 ml (0.03 mol) of trimethylsilylcyanide in 20 ml of dry benzene was treated with 0.44 gm (0.001 mol) zinc iodide and 4.63 ml (0.028 mol) of benzophenoneimine. The reaction mixture was stirred at room temperature for 10 min., whereupon a white precipitate formed. The reaction mixture was quenched with wet ether and stirred for 2 hours. The liquid phase was washed with saturated brine solution and dried over sodium sulfate and evaporated in vacuo. The residue was recrystallized from ether-hexane to afford 2.4 gm (38%). 1H NMR (CDCl3, 300 MHz) δ 7.7-7.6 (m, 4H), 7.4-7.28 (m, 6H); 13C NMR (CDCl3, 75.5 MHz ) δ 141.2, 128.9, 128.6, 125.8, 123.4, 60.8.

Workup

  1. customformed
  2. customThe reaction mixture was quenched with wet ether
  3. stirringstirred for 2 hours
  4. washThe liquid phase was washed with saturated brine solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from ether-hexane
  8. customto afford 2.4 gm (38%)

Sources & evidence

ORD record
ord-ae157c7aa2ad4e5eb866f60ccca6ce39
Source dataset
uspto-grants-1996_05
Patent number
US05521220

Reaction notes

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