Aluminium lithium hydride → 2-[2-(4-Bromo-phenyl)-ethanesulfonylamino]-5-hydroxymethyl-benzenesulfonamide

HRID 2283357Notes

Reaction equation

HRID 2283357 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][S:16]([NH:19][C:20]2[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][C:21]=2[S:29](=[O:32])(=[O:31])[NH2:30])(=[O:18])=[O:17])=[CH:10][CH:9]=1>O1CCCC1>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][S:16]([NH:19][C:20]2[CH:28]=[CH:27][C:23]([CH2:24][OH:25])=[CH:22][C:21]=2[S:29]([NH2:30])(=[O:32])=[O:31])(=[O:17])=[O:18])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 577510934-[2-(4-Bromo-phenyl)-ethanesulfonylamino]-3-sulfamoyl-benzoic acid

Product 1

HCID 577510512-[2-(4-Bromo-phenyl)-ethanesulfonylamino]-5-hydroxymethyl-benzenesulfonamideYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1 M in tetrahydrofuran, 1.9 mL, 1.9 mmol) was added dropwise to a solution of 4-[2-(4-bromo-phenyl)-ethanesulfonylamino]-3-sulfamoyl-benzoic acid (0.22 g, 0.47 mmol) in anhydrous tetrahydrofuran (20 mL) at 0° C. The reaction mixture was stirred at room temperature for 5 hours, cooled to 0° C. and quenched by addition of saturated sodium sulfate solution (20 mL). The precipitate was removed by filtration and the filtrate was extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to give 0.15 g (71% yield) of the title compound.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by addition of saturated sodium sulfate solution (20 mL)
  3. customThe precipitate was removed by filtration
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4537825eca84eab993db1b97581ab3e
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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