4-Acetylbenzenesulphonamide → HCID 49787460, compound

HRID 1173045Notes

Reaction equation

HRID 1173045 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](N)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:14]([Si](C)(C)C)([F:17])([F:16])[F:15].O.[F-].C([N+:28]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:33][CH2:34]CC)CCCC)CCC>C1COCC1.C([O-])(O)=O.[Na+]>[F:15][C:14]([F:17])([F:16])[C:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([N:28]2[CH2:33][CH2:34][CH2:40][CH2:39][CH2:38][CH2:37]2)(=[O:12])=[O:11])=[CH:8][CH:9]=1)([OH:3])[CH3:2]

Participants

6

Reactant 3

HCID 740654-AcetylbenzenesulphonamideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrate

Product 1

HCID 49787460HCID 49787460, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

The 4-acetylbenzenesulfonamide prepared above (247 mg, 0.879 mmol, 1.0 equiv) was dissolved in 10 mL THF followed by the addition on 3.52 mL of a 0.5M solution of CF3TMS in THF. After 5 min, 229 mg of tetrabutylammonium fluoride hydrate (0.879 mmol, 1.0 equiv) was added to the stirring solution. After stirring 21 h the reaction mixture was diluted with sat. NaHCO3, extracted (2× EtOAc), dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography (SiO2, 2% MeOH/CH2Cl2) gave the product as a white solid. 1H NMR (DMSO, 400 MHz) δ 7.80 (s, 4H), 6.84 (s, 1H), 3.21 (t, J=5.8 Hz, 4H), 1.71 (s, 3H), 1.63 (m, 4H), 1.50 (m, 4H).

Workup

  1. extractionextracted (2× EtOAc)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography (SiO2, 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4c2c0d59a0764e08b28dce74e504fb4a
Source dataset
uspto-grants-2010_11
Patent number
US07834047B2

Reaction notes

Loading…