Methyl 4-chloro-3-sulfamoylbenzoate → 2-chloro-5-(hydroxymethyl)Benzenesulfonamide

HRID 734734Notes

Reaction equation

HRID 734734 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[Cl:15])[C:8](OC)=[O:9])(=[O:4])=[O:3].[Cl-].[Cl-].[Ca+2].[BH4-].[Na+]>C1COCC1.CCO>[Cl:15][C:14]1[CH:13]=[CH:12][C:7]([CH2:8][OH:9])=[CH:6][C:5]=1[S:2]([NH2:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 4277179Methyl 4-chloro-3-sulfamoylbenzoateHCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

Product 1

HCID 183743812-chloro-5-(hydroxymethyl)BenzenesulfonamideYield 83%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of methyl 3-(aminosulfonyl)-4-chlorobenzoate (950 mg, 3.8 mmol) in THF/EtOH (40 mL, 1:1), CaCl2 (843 mg, 7.6 mmol) and NaBH4 (575 mg, 15.2 mmol) were added in one portion respectively. The reaction mixture was stirred at room temperature for 6 hours, then quenched with water. 1 M aqueous citric acid (10 mL) was added to the mixture and extracted with EtOAc (3×100 mL). The extracts were combined, washed with brine, and dried (Na2SO4). The solvent was evaporated to afford the product (696 mg, 83%) as a white solid. MS (ES+) m/z 244 [M+Na]+.

Workup

  1. customquenched with water
  2. addition1 M aqueous citric acid (10 mL) was added to the mixture
  3. extractionextracted with EtOAc (3×100 mL)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1f1c3af252b54e78b0946e2220a3bb55
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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