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

HRID 1943849Notes

Reaction equation

HRID 1943849 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-f147378c989f45359b038974dd319569
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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