Sodium Hydroxide → 2,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acid

HRID 2196630Notes

Reaction equation

HRID 2196630 reaction equation
[OH-].[Na+].[F:3][C:4]1[C:13]([N:14](S(CCC)(=O)=O)[S:15]([CH2:18][CH2:19][CH3:20])(=[O:17])=[O:16])=[CH:12][CH:11]=[C:10]([F:27])[C:5]=1[C:6]([O:8]C)=[O:7]>C1COCC1.CO>[F:3][C:4]1[C:13]([NH:14][S:15]([CH2:18][CH2:19][CH3:20])(=[O:16])=[O:17])=[CH:12][CH:11]=[C:10]([F:27])[C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58095328HCID 58095328, compound

Product 1

HCID 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acidYield 77%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 1N aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were then removed in vacuo (water bath temperature 35° C.). 1N HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4×50 mL). The material was then washed with Et2O (4×15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77% yield). 1H NMR (400 MHz, d6-DMSO) δ 9.74 (s, 1H), 7.57-7.50 (m, 1H), 7.23-7.17 (m, 1H), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J=7.4 Hz, 3H). m/z (APCI-neg) M−1=278.0.

Workup

  1. customThe majority of the organic solvents were then removed in vacuo (water bath temperature 35° C.)
  2. addition1N HCl (150 mL) was slowly added to the mixture
  3. filtrationthe resulting solid was filtered
  4. washrinsed with water (4×50 mL)
  5. washThe material was then washed with Et2O (4×15 mL)

Sources & evidence

ORD record
ord-73e19adcb05b41449ec28ead8e734950
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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