Sodium Bicarbonate → N-(2-chloro-4-hydroxy-benzyl)-N-[4-(3-hydroxy-propyl)-phenyl]-2,4,6-trimethyl-benzenesulfonamide

HRID 1827595Notes

Reaction equation

HRID 1827595 reaction equation
[Cl:1][C:2]1[CH:31]=[C:30]([OH:32])[CH:29]=[CH:28][C:3]=1[CH2:4][N:5]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH:26]=[O:27])=[CH:20][CH:19]=1)[S:6]([C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[CH3:17])(=[O:8])=[O:7].[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:31]=[C:30]([OH:32])[CH:29]=[CH:28][C:3]=1[CH2:4][N:5]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][OH:27])=[CH:20][CH:19]=1)[S:6]([C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[CH3:17])(=[O:8])=[O:7]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 22137388N-(2-chloro-4-hydroxy-benzyl)-2,4,6-trimethyl-N-[4-(3-oxo-propyl)-phenyl]-benzenesulfonamide

Product 1

HCID 22137350N-(2-chloro-4-hydroxy-benzyl)-N-[4-(3-hydroxy-propyl)-phenyl]-2,4,6-trimethyl-benzenesulfonamideYield 47.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-chloro-4-hydroxy-benzyl)-2,4,6-trimethyl-N-[4-(3-oxo-propyl)-phenyl]-benzenesulfonamide (0.036 g, 0.08 mmol) in 0.2 mL methanol and 0.2 mL methylene chloride was added sodium borohydride (0.014 g, 0.38 mmol). The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the aqueous solution was washed with methylene chloride. The organic layer was dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography (40% ethyl acetate/hexanes) afforded 0.018 g of N-(2-chloro-4-hydroxy-benzyl)-N-[4-(3-hydroxy-propyl)-phenyl]-2,4,6-trimethyl-benzenesulfonamide. MS 474.0 (M+1)+

Workup

  1. washthe aqueous solution was washed with methylene chloride
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d2edf6000da34aef9f243e7a0ad0698c
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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