1,2-Dibromoethane → HCID 22137407, compound

HRID 1827557Notes

Reaction equation

HRID 1827557 reaction equation
[OH: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][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[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.[Br:35][CH2:36][CH2:37]Br.[OH-].[Na+]>O>[Br:35][CH2:36][CH2:37][O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[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:6][CH:7]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 22137324HCID 22137324, compound

Product 1

HCID 22137407HCID 22137407, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension of N-(4-hydroxy-phenyl)-2,4,6-trimethyl-N-[3-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide (0.238 g, 0.49 mmol) and 1,2-dibromoethane (0.43 mL, 4.94 mmol) in 1 mL water was added sodium hydroxide (0.020 g, 0.49 mmol, dissolved in 0.1 mL of water). The reaction mixture was heated at reflux for 3 hr. and was cooled to room temperature. The reaction mixture was diluted with 10 mL water and the aqueous solution was washed with ethyl acetate (3×15 mL). The combined organic layers were washed with saturated aqueous sodium chloride, dried (magnesium sulfate), and concentrated. Medium pressure silica gel chromatography (25% ethyl acetate/hexanes) afforded 0.075 g of the title compound of Step E.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hr
  3. washthe aqueous solution was washed with ethyl acetate (3×15 mL)
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e420667da3ec4423ae8ae3f65ef0cdab
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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