Water → HCID 68292321, compound

HRID 339909Notes

Reaction equation

HRID 339909 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11](=[O:25])(=[O:24])[NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:23][O:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][S:11]([CH2:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][CH:6]=1)(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68292257HCID 68292257, compound

Product 1

HCID 68292321HCID 68292321, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(2,4-dimethoxybenzylsulfamoyl)methyl]benzoic acid methyl ester (6 g) in THF (300 ml) was added, at 0° C., lithium aluminum hydride (1.5 g) in portions, and the mixture was stirred at room temperature for 1 h. Then water (9 ml), 6 M NaOH (7 ml) and water again (27 ml) were added successively. The solids were filtered off and dichloromethane was added to the filtrate. The organic phase was removed, dried over magnesium sulfate and concentrated. This gave the product (6 g) with a molecular weight of 351.4 g/mol (C17H21NO5S).

Workup

  1. filtrationThe solids were filtered off
  2. additiondichloromethane was added to the filtrate
  3. customThe organic phase was removed
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-febf5676a9cc4e71ba5560931e8f10f7
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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