Hydrochloric Acid → N-(2-Chloro-4-hydroxy-benzyl)-N-(4-iodo-phenyl)-2,4,6-trimethyl-benzenesulfonamide

HRID 1827571Notes

Reaction equation

HRID 1827571 reaction equation
[Cl:1][C:2]1[CH:28]=[C:27]([O:29]C2CCCCO2)[CH:26]=[CH:25][C:3]=1[CH2:4][N:5]([C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=1)[S:6]([C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[CH3:17])(=[O:8])=[O:7].Cl.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1.CO.O1CCOCC1>[Cl:1][C:2]1[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:3]=1[CH2:4][N:5]([C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][CH:19]=1)[S:6]([C:9]1[C:10]([CH3:17])=[CH:11][C:12]([CH3:16])=[CH:13][C:14]=1[CH3:15])(=[O:8])=[O:7]

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 22137336N-[2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-N-(4-iodo-phenyl)-2,4,6-trimethyl-benzenesulfonamide

Product 1

HCID 22137423N-(2-Chloro-4-hydroxy-benzyl)-N-(4-iodo-phenyl)-2,4,6-trimethyl-benzenesulfonamideYield 72%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of N-[2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-N-(4-iodo-phenyl)-2,4,6-trimethyl-benzenesulfonamide (1.13 g, 1.80 mmol) in 1 mL tetrahydrofuran and 2 mL methanol was added HCl (4.5 mL of a 4.0 M solution in 1,4-dioxane, 18.05 mmol) and triethylsilane (2.88 mL, 18.05 mmol). The reaction mixture was stirred at room temperature overnight. Additional HCl (1 mL of a 4.0 M solution in 1,4-dioxane, 4 mmol) was added and the reaction mixture was stirred at room temperature for 2 days. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with methylene chloride. The organic layer was dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography of the residue (methylene chloride) afforded 0.70 g (72%) of the title compound of Step C.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 days
  2. extractionthe mixture was extracted with methylene chloride
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0af9d1e743e945e697a9f39112f2570e
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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