Hydrochloric Acid → HCID 22137278, compound

HRID 1827574Notes

Reaction equation

HRID 1827574 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28]C3CCCCO3)[CH:23]=2)[S:9]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])(=[O:11])=[O:10])=[CH:4][CH:3]=1.Cl.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1.O1CCOCC1>[OH:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][N:8]([C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=1)[S:9]([C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[CH3:20])(=[O:11])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 22137311HCID 22137311, compound

Product 1

HCID 22137278HCID 22137278, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(4-iodo-phenyl)-2,4,6-trimethyl-N-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide (0.506 g, 0.86 mmol) in 5 mL tetrahydrofuran was added HCl (5.35 mL of a 4.0 M solution in 1,4-dioxane, 21.4 mmol) and triethylsilane (1.37 mL, 8.56 mmol). The reaction mixture was stirred at room temperature overnight. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with methylene chloride. The organic layer was separated and concentrated. Medium pressure silica gel chromatography of the residue (methylene chloride) afforded 0.36 g (83%) of the title compound of Step C.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. customThe organic layer was separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-51c8cd172cb946b1a88a688bb3216ed9
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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