Lithium borohydride → 2-chloro-5-(hydroxymethyl)Benzenesulfonamide

HRID 1810141Notes

Reaction equation

HRID 1810141 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([S:12](=[O:15])(=[O:14])[NH2:13])[CH:6]=1)C.[BH4-].[Li+]>O1CCCC1.O>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][OH:3])=[CH:6][C:7]=1[S:12]([NH2:13])(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 15938945Benzoic acid, 3-(aminosulfonyl)-4-chloro-, ethyl ester

Product 1

HCID 183743812-chloro-5-(hydroxymethyl)BenzenesulfonamideYield 88.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
4 °C

Procedure

To a solution of 4-chloro-3-sulfamoyl-benzoic acid ethyl ester (46.95 g, 166 mmol) in 500 mL of dry tetrahydrofuran is added dropwise, with stirring, 199 mL of a 2 M solution of lithium borohydride in tetrahydrofuran. The mixture is stirred and refluxed for 5 hr, then left at room temperature for 18 h, and is then carefully diluted with 400 mL of water. The mixture is cooled to 4° C. for 24 hours and filtered to yield 32.7 g (82%) of the title compound as an off-white solid.

Workup

  1. stirringThe mixture is stirred
  2. temperaturerefluxed for 5 hr
  3. filtrationfiltered

Sources & evidence

ORD record
ord-dff4cfd8504643c99a790be4f741a556
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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