Potassium Carbonate → HCID 52950736, compound

HRID 80403Notes

Reaction equation

HRID 80403 reaction equation
[F:1][C:2]([F:15])([C:11]([F:14])([F:13])[F:12])[CH2:3][CH2:4][S:5]([CH2:8][C:9]#[N:10])(=[O:7])=[O:6].[F:16][C:17]([S:20][CH2:21][CH2:22]OS(C(F)(F)F)(=O)=O)([F:19])[F:18].C([O-])([O-])=O.[K+].[K+]>COCCOC.O>[F:15][C:2]([F:1])([C:11]([F:12])([F:13])[F:14])[CH2:3][CH2:4][S:5]([CH:8]([CH2:22][CH2:21][S:20][C:17]([F:19])([F:18])[F:16])[C:9]#[N:10])(=[O:6])=[O:7]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 252420282-(Trifluoromethylthio)ethyl TrifluoromethanesulfonateHCID 57425691(3,3,4,4,4-Pentafluorobutylsulfonyl)acetonitrile

Product 1

HCID 52950736HCID 52950736, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (3,3,4,4,4-Pentafluoro-butane-1-sulfonyl)-acetonitrile (WO2007/060839) (0.50 g, 1.99 mmol), trifluoro-methanesulfonic acid 2-trifluoromethylsulfanyl-ethyl ester (WO 2007/147888) (0.55 g, 1.99 mmol), and K2CO3 (0.82 g, 5.97 mmol) in 1,2-dimethoxyethane (20 mL) was stirred under nitrogen at room temperature overnight. The reaction mixture was diluted with H2O (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, hexanes/EtOAc 19:1) to afford compound II-1 (0.28 g, 37%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic extracts were washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (SiO2, hexanes/EtOAc 19:1)
  6. customto afford compound II-1 (0.28 g, 37%) as a white solid

Sources & evidence

ORD record
ord-1bf14432504f4839beb54d5528a54b3b
Source dataset
uspto-grants-2014_09
Patent number
US08846569B2

Reaction notes

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