Sodium Iodide → 4-Cyano-5-methyl-4-(3-cyano-2-thienyl)hexyl iodide

HRID 1071632Notes

Reaction equation

HRID 1071632 reaction equation
[C:1]([C:3]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[C:16]#[N:17])([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][CH:13]=[CH:14][C:15]=1[C:16]#[N:17])([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 223936344-Cyano-5-methyl-4-(3-cyano-2-thienyl)hexanol

Product 1

HCID 223938264-Cyano-5-methyl-4-(3-cyano-2-thienyl)hexyl iodideYield 95.1%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

244 mg (0.98 mmol) of 4-cyano-5-methyl-4-(3-cyano-2-thienyl)hexanol was dissolved in 10 ml of acetonitrile and 0.16 ml (1.18 mmol) of triethylamine, and 83.6 μl (108 mmol) of mesyl chloride was added thereto. After about 5 minutes, 1.47 g (9.80 mmol) of sodium iodide was added. After completion of the reaction, brine and ethyl acetate were added, and the ethyl acetate layer was washed with an aqueous sodium thiosulfate aqueous solution and brine, dried over anhydrous magnesium sulfate and evaporated, to give a crude product. The crude product was subjected to silica gel (eluted at ethyl acetate:hexane=1:10), to give 334 mg (0.93 mmol, 95.1%) of the title compound as a yellow oil.

Workup

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

Sources & evidence

ORD record
ord-b6ea499660b24c42b2a23b466c9f051e
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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