Triethylamine → HCID 69036753, compound

HRID 2251264Notes

Reaction equation

HRID 2251264 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[S:10]([OH:12])=[O:11].FC1C(F)=C(F)C=CC=1S(Cl)(=O)=O.C(N(CC)CC)C.[Cl:33][CH2:34][CH2:35][CH2:36]I>CN(C=O)C>[Cl:33][CH2:34][CH2:35][CH2:36][S:10]([C:3]1[CH:4]=[CH:5][C:6]([F:9])=[C:7]([F:8])[C:2]=1[F:1])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 813631-Chloro-3-iodopropaneHCID 27769772,3,4-Trifluorobenzenesulfonyl chlorideHCID 50998774HCID 50998774, compound

Product 1

HCID 69036753HCID 69036753, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 30.6 mmol 2,3,4-trifluoro-benzenesulfinic acid (acid (prepared in analogy to example 2.20(a) from 2,3,4-trifluoro-benzenesulfonyl chloride) and 91.8 mmol triethylamine in 20 ml DMF was added 61.2 mmol 1-chloro-3-iodopropane, and the mixture stirred at room temperature for 1 h. The reaction mixture was then poured onto water and extracted three times with ethyl acetate. The combined organic phases were then washed twice with saturated aq. NaCl solution, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed on silica gel (eluant: ethyl acetate/heptane 1:4) to afford the title compound. MS (m/e): 275.2 ({37Cl}M+H+, 33%), 273.1({35Cl}M+H+, 100%),

Workup

  1. additionThe reaction mixture was then poured onto water
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic phases were then washed twice with saturated aq. NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel (eluant: ethyl acetate/heptane 1:4)

Sources & evidence

ORD record
ord-36586f0a3538411abe391d143cb68acd
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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