Triethylamine → HCID 12993966, compound

HRID 351796Notes

Reaction equation

HRID 351796 reaction equation
[F:1][C:2](=[C:12]([F:14])[F:13])[CH2:3][CH2:4][S:5][CH:6]1[NH:10][C:9](=[O:11])[CH2:8][O:7]1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>O1CCCC1>[CH3:22][S:23]([O:11][C:9]1[N:10]=[C:6]([S:5][CH2:4][CH2:3][C:2]([F:1])=[C:12]([F:13])[F:14])[O:7][CH:8]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22714642HCID 22714642, compound

Product 1

HCID 12993966HCID 12993966, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1 g of 2-(3,4,4-trifluoro-3-butenylthio)oxazolidin-4-one and 0.9 g of triethylamine were dissloved in 30 ml of tetrahydrofuran, to which 0.56 g of methanesulfonic chloride was added dropwise under ice cooling and stirred at 50° C. for 8 hours. After distilling off the solvent under reduced pressure, the residue was dissolved in ether. After washing with 1N hydrochloric acid and water, it was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (eluent: hexane:dichloromethane=1:1) to obtain 0.25 g of 4-methylsulfonyloxy-2-(3,4,4-trifluoro-3-butenylthio)oxazole (yield 19%). n20D=1.4830.

Workup

  1. additionwas added dropwise under ice cooling
  2. distillationAfter distilling off the solvent under reduced pressure
  3. dissolutionthe residue was dissolved in ether
  4. washAfter washing with 1N hydrochloric acid and water, it
  5. dry with materialwas dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by column chromatography (eluent: hexane:dichloromethane=1:1)

Sources & evidence

ORD record
ord-79af85afebbc4c1383be7f3e4a832a82
Source dataset
uspto-grants-2004_06
Patent number
US06743814B2

Reaction notes

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