Sodium Hydroxide → 4-{[(Methylsulfonyl)amino]methyl}benzoic acid

HRID 1776558Notes

Reaction equation

HRID 1776558 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[OH-].[Na+].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C1COCC1>[CH3:14][S:15]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 15066094-{[(Methylsulfonyl)amino]methyl}benzoic acidYield 32.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(aminomethyl)benzoic acid (4 g, 26.5 mmol) and NaOH 1M (52.9 ml, 52.9 mmol) in THF (60 ml), methanesulfonyl chloride (2.474 ml, 31.8 mmol) was slowly added and the reaction was stirred at RT overnight. The mixture was acidified and extracted twice with EtOAc; the combined organic layers were washed with brine, dried over Na2SO4 and evaporated to dryness. The resulting solid was suspended in MeOH (120 ml) and stirred overnight. The precipitate was collected by filtration to give 4-(methylsulfonamidomethyl)-benzoic acid (1.99 g, 8.68 mmol, 32.8% yield, MS/ESI+ 229.9 [MH]+).

Workup

  1. extractionextracted twice with EtOAc
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. stirringstirred overnight
  6. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-ff629c6959e749f897475c0f241eaa22
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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