Sodium Iodide → 4-Cyano-4-(5-cyano-2-thienyl)-5-methylhexyl iodide

HRID 1071633Notes

Reaction equation

HRID 1071633 reaction equation
[C:1]([C:3]([C:11]1[S:12][C:13]([C:16]#[N:17])=[CH:14][CH:15]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6]O)#[N:2].C(N(CC)CC)C.S(Cl)(C)(=O)=O.[I-:30].[Na+]>C(#N)C.[Cl-].[Na+].O.C(OCC)(=O)C>[C:1]([C:3]([C:11]1[S:12][C:13]([C:16]#[N:17])=[CH:14][CH:15]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6][I:30])#[N:2]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 223936354-Cyano-4-(5-cyano-2-thienyl)-5-methylhexanol

Product 1

HCID 223937304-Cyano-4-(5-cyano-2-thienyl)-5-methylhexyl iodideYield 91.7%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

1.05 g (4.23 mmol) of 4-cyano-5-methyl-4-(5-cyano-2-thienyl)hexanol was dissolved in 40 ml of acetonitrile and 0.80 ml (5.71 mmol) of triethylamine. 0.39 ml (5.07 mmol) of mesyl chloride was added thereto. After about 0.10 minutes, 6.34 g (42.3 mmol) of sodium iodide was added. After completion of the reaction, brine and ethyl acetate were added. The ethyl acetate layer was washed with an aqueous sodium thiosulfate and brine, dried over magnesium sulfate and evaporated, to give a crude product. The crude product was subjected to silica gel (eluted with ethyl acetate:hexane=1:2), to give 1.39 g (3.88 mmol, 91.7%) of the title compound as a yellow oil.

Workup

  1. additionwere added
  2. washThe ethyl acetate layer was washed with an aqueous sodium thiosulfate and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give a crude product

Sources & evidence

ORD record
ord-2ad95245a6894b0eae18ea9287392762
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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