Sodium Iodide → HCID 12993973, compound

HRID 351801Notes

Reaction equation

HRID 351801 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.[CH3:16][S-:17].[Na+].[I-].[Na+].CN(C)C=O>O>[CH3:16][S:17][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

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 12993972HCID 12993972, compound

Product 1

HCID 12993973HCID 12993973, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1.2 g of 4-chloromethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole, 0.5 g of sodium thiomethoxide and 0.1 g of sodium iodide were added to 20 ml of dimethylformamide (hehydrated) and stirred at 80° C. for 10 hours. After cooling, 200 ml of water were 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-methylthiomethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole as colorless oil (yield 23.9%). n20D=1.5099.

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-31e92d10e04e4842915589ce641362c4
Source dataset
uspto-grants-2004_06
Patent number
US06743814B2

Reaction notes

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