Hydrochloric Acid → HCID 87462555, compound

HRID 534692Notes

Reaction equation

HRID 534692 reaction equation
[C:1]1([S:7]([C:10]([C:13]([S:16](F)(=[O:18])=[O:17])([F:15])[F:14])([F:12])[F:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>ClCCCl>[CH2:20]([NH:27][S:16]([C:13]([F:15])([F:14])[C:10]([S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])([F:12])[F:11])(=[O:18])=[O:17])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 23726270HCID 23726270, compound2×

Product 1

HCID 87462555HCID 87462555, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Added to a solution of 1,2-dichloroethane (5 ml), containing the PhSO2CF2CF2SO2F (325 mg, 1 mmol) prepared according to the method from example 4, was freshly distilled benzylamine (550 μl, 5 mmol). The mixture was stirred and heated at 50° C. for 20 h until the disappearance of PhSO2CF2CF2SO2F (monitored by TLC and 19F NMR/CDCl3). After returning to ambient temperature, an aqueous solution of HCl (10%) was added to the reaction medium. The aqueous and organic phases were separated and the aqueous phase was extracted with dichloromethane. The organic phases were combined and dried over MgSO4. After filtration and evaporation of the solvents, the residue was purified by chromatography over silica gel (pentane to pentane/AcOEt:4/1). The sulfonamide product was obtained in the form of a white solid (340 mg, 83%).

Workup

  1. customprepared
  2. customAfter returning to ambient temperature
  3. customThe aqueous and organic phases were separated
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration and evaporation of the solvents
  7. customthe residue was purified by chromatography over silica gel (pentane to pentane/AcOEt:4/1)

Sources & evidence

ORD record
ord-dd6bc3b71e3d462f8d43b84b40bbc390
Source dataset
uspto-grants-2014_10
Patent number
US08853448B2

Reaction notes

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