Benzenesulfonyl chloride → HCID 22137317, compound

HRID 1827567Notes

Reaction equation

HRID 1827567 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16]C3CCCCO3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[OH:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:8]([C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=2)[S:36]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:38])=[O:37])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 22137416HCID 22137416, compound

Product 1

HCID 22137317HCID 22137317, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-iodo-phenyl)-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amine (3.43 g, 8.38 mmol) in 10 mL methylene chloride was added triethylamine (2.0 mL, 14.35 mmol) and benzenesulfonyl chloride (1.2 mL, 9.40 mmol). The reaction mixture was stirred at room temperature for 24 hr. The reaction mixture was quenched with water, was acidified with 1N HCl, and the aqueous solution was washed three times with methylene chloride. The combined organic extracts were washed with saturated aqueous sodium bicarbonate, dried (magnesium sulfate), filtered, and concentrated. The residue was dissolved in methanol and the solution was treated with a catalytic amount of 1N HCl. The reaction mixture was stirred at room temperature for 20 hr. The reaction mixture was made basic with saturated aqueous sodium bicarbonate and the aqueous solution was washed two times with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography (10% ethyl acetate/hexanes to 20% ethyl acetate/hexanes) afforded 3.21 g (82%) of the title compound of Step B.

Workup

  1. customThe reaction mixture was quenched with water
  2. washthe aqueous solution was washed three times with methylene chloride
  3. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in methanol
  8. additionthe solution was treated with a catalytic amount of 1N HCl
  9. stirringThe reaction mixture was stirred at room temperature for 20 hr
  10. washthe aqueous solution was washed two times with methylene chloride
  11. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-826d016666b84166ac4a77978c4642e8
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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