Hydrochloric Acid → 6-Chloro-2-fluoro-3-(propane-1-sulfonamido)benzoic acid

HRID 2196635Notes

Reaction equation

HRID 2196635 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])=[C:6]([F:18])[C:5]([N:19](S(CCC)(=O)=O)[S:20]([CH2:23][CH2:24][CH3:25])(=[O:22])=[O:21])=[CH:4][CH:3]=1.Cl>C1COCC1.[OH-].[K+]>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([F:18])[C:5]([NH:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:21])=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58095375Phenylmethyl 3-[bis(propylsulfonyl)amino]-6-chloro-2-fluorobenzoate

Product 1

HCID 580875006-Chloro-2-fluoro-3-(propane-1-sulfonamido)benzoic acidYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14797Potassium HydroxideSolvent

Procedure

Benzyl 6-chloro-2-fluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (5.4 g, 10.98 mmol) was dissolved in THF (100 mL) and 1M aqueous KOH (100 mL). This mixture was refluxed for 16 hours and then allowed to cool to room temperature. The mixture was then acidified to a pH of 2 with 2M aqueous HCl and extracted with EtOAc (2 X). The extracts were washed with water, dried over sodium sulfate and concentrated to a solid that was triturated with hexanes/ether to give 6-chloro-2-fluoro-3-(propylsulfonamido)benzoic acid (2.2 g, 68%) as a solid. NMR (DMSO-d6, 400 MHz) δ 9.93 (s, 1H), 7.49 (t, 1H, J=8), 7.38 (dd, 1H, J=8, 2), 3.11-3.16 (m, 2H), 1.68-1.78 (m, 2H), 0.97 (t, 3H, J=8).

Workup

  1. temperatureThis mixture was refluxed for 16 hours
  2. extractionextracted with EtOAc (2 X)
  3. washThe extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to a solid
  6. customthat was triturated with hexanes/ether

Sources & evidence

ORD record
ord-eee9cb5228414b8284217c344e2828b6
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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