4-(Trifluoromethyl)benzenesulfonyl chloride → HCID 11327500, compound

HRID 1841591Notes

Reaction equation

HRID 1841591 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1.[F:16][C:17]([F:29])([F:28])[C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>O1CCOCC1>[CH3:15][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][S:24]([C:21]2[CH:20]=[CH:19][C:18]([C:17]([F:16])([F:28])[F:29])=[CH:23][CH:22]=2)(=[O:26])=[O:25])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 11458449HCID 11458449, compound

Product 1

HCID 11327500HCID 11327500, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.26 (6.03 mmol) of 4-(4-Dimethylamino-butoxy)-phenylamine in 15 ml dioxane was treated with 1.13 ml (6.1 mmol) Hünigsbase and 1.86 g (7.59 mmol) 4-(trifluoromethyl)benzenesulfonyl chloride. The reaction mixture was stirred over night at room temperature and extracted with aqueous saturated NaHCO3 solution/EtOAc (3×). The organic phase was dried over Na2SO4 and evaporated. The residue (partially disulfonamide) was dissolved in 20 ml dioxane, treated with 11.1 ml 1N NaOH and heated for 1 h at 100° C. The reaction mixture was neutralized (pH 7 with 1 N HCl) and extracted with EtOAc (2×). The organic phase was washed with aqueous saturated NaHCO3, dried over Na2SO4 and evaporated to yield 2.1 g (84%) of N-[4-(4-Dimethylamino-butoxy)-phenyl]-4-trifluoromethyl-benzenesulfonamide, MS: 417 (MH+).

Workup

  1. extractionextracted with aqueous saturated NaHCO3 solution/EtOAc (3×)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. dissolutionThe residue (partially disulfonamide) was dissolved in 20 ml dioxane
  5. additiontreated with 11.1 ml 1N NaOH
  6. temperatureheated for 1 h at 100° C
  7. extractionextracted with EtOAc (2×)
  8. washThe organic phase was washed with aqueous saturated NaHCO3
  9. dry with materialdried over Na2SO4
  10. customevaporated

Sources & evidence

ORD record
ord-701858db21bf426f8b120a35baa4d4df
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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