Sodium Iodide → HCID 12993975, compound

HRID 351803Notes

Reaction equation

HRID 351803 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([S:8][CH2:9][CH2:10][C:11]([F:15])=[C:12]([F:14])[F:13])[O:6][CH:7]=1.[C-:16]#[N:17].[K+].C1OCCOCCOCCOCCOCCOC1.[I-].[Na+]>O.CN(C)C=O>[C:16]([CH2:2][C:3]1[N:4]=[C:5]([S:8][CH2:9][CH2:10][C:11]([F:15])=[C:12]([F:14])[F:13])[O:6][CH:7]=1)#[N:17]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 12993972HCID 12993972, compound

Product 1

HCID 12993975HCID 12993975, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.2 g of 4-chloromethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole, 1 g of potassium cyanide, 0.1 g of 18-crown-6-ether and 0.1 g of sodium iodide were added to 20 ml of dimethylformamide (dehydrated) and stirred at 100° C. for 20 hours. After cooling, 200 ml of water was added to the reaction mixture and extracted with 100 ml of diethyl ether twice. The extracted diethyl ether layers were put together, washed with 200 ml of water, dried with magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (eluent: hexane:dichloromethane=2:1) to obtain 0.3 g of 4-cyanomethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole as colorless oil (yield 15.6%). n20D=1.4844.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 100 ml of diethyl ether twice
  3. washwashed with 200 ml of water
  4. dry with materialdried with magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography (eluent: hexane:dichloromethane=2:1)

Sources & evidence

ORD record
ord-2297770901e440f282cb1b1a28288784
Source dataset
uspto-grants-2004_06
Patent number
US06743814B2

Reaction notes

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