Trifluoroacetic acid → HCID 21476635, compound

HRID 2293292Notes

Reaction equation

HRID 2293292 reaction equation
C([N:8](CC1C=CC=CC=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18](=[C:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([F:26])[CH:20]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])C1C=CC=CC=1.FC(F)(F)C(O)=O>O>[C:27]1(=[C:18]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([F:26])[CH:20]=2)[C:15]2[CH:14]=[CH:13][C:12]([S:9]([NH2:8])(=[O:10])=[O:11])=[CH:17][CH:16]=2)[CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15411268HCID 15411268, compound

Product 1

HCID 21476635HCID 21476635, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 6.5 g of N,N-dibenzyl-4-[(cyclopentylidene)(3-fluoro-4-methylphenyl)methyl]benzenesulfonamide, prepared in Example 10, in ml of trifluoroacetic acid is heated for 10 hours at 60° C. The mixture is poured into iced water and extracted with dichloromethane. The organic phase is washed with sodium bicarbonate solution, dried over magnesium sulfate and evaporated under vacuum. The residue is chromatographed on silica gel in a dichloromethane/acetone mixture (95/5) to give 3 g of 4-[(cyclopentylidene)(3-fluoro-4-methylphenyl)methyl]benzenesulfonamide in the form of a semicrystalline oil.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase is washed with sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum
  5. customThe residue is chromatographed on silica gel in a dichloromethane/acetone mixture (95/5)

Sources & evidence

ORD record
ord-f805e9fd91ea40e0852598b5baeec1a7
Source dataset
uspto-grants-1997_11
Patent number
US05686460

Reaction notes

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