Hydrochloric Acid → 2-Chloro-6-fluoro-3-(propylsulfonamido)benzoic acid
Reaction equation
[Cl:1][C:2]1[C:17]([NH:18][S:19]([CH2:22][CH2:23][CH3:24])(=[O:21])=[O:20])=[CH:16][CH:15]=[C:14]([F:25])[C:3]=1[C:4]([O:6]CC1C=CC=CC=1)=[O:5].[OH-].[Ba+2].[OH-].Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[C:17]([NH:18][S:19]([CH2:22][CH2:23][CH3:24])(=[O:20])=[O:21])=[CH:16][CH:15]=[C:14]([F:25])[C:3]=1[C:4]([OH:6])=[O:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
Benzyl 2-chloro-6-fluoro-3-(propylsulfonamido)benzoate (174.5 mg, 0.4523 mmol) was dissolved in 3:1 dioxane:water (7.5 mL) and treated with barium hydroxide (100.7 mg, 0.5879 mmol). The reaction mixture was heated to 80° C. for 16 hours and then allowed to cool to ambient temperature. The mixture was acidified to a pH of 0 with concentrated HCl. The reaction mixture was allowed to stir for 10 minutes, after which the pH was adjusted to a pH of 4 using saturated sodium bicarbonate. The mixture was extracted with EtOAc (2×). The extracts were washed with water (2×) and brine (1×), dried over sodium sulfate, and concentrated to afford 2-chloro-6-fluoro-3-(propylsulfonamido)benzoic acid (75.7 mg, 0.2560 mmol, 56.6% yield). MS (APCI-neg) m/z=293.9 (M-H).
Workup
- temperatureto cool to ambient temperature
- extractionThe mixture was extracted with EtOAc (2×)
- washThe extracts were washed with water (2×) and brine (1×)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3e5c755fa0ba4083ac231edaceca1e6f
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338452B2
Reaction notes
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