Sodium Carbonate → 2-Fluoro-5-(propylsulfonamido)benzoic acid
Reaction equation
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2][CH3:3].C([O-])([O-])=O.[Na+].[Na+].[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:24])=[C:19]([CH:23]=1)[C:20]([OH:22])=[O:21]>O>[F:24][C:18]1[CH:17]=[CH:16][C:15]([NH:14][S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])=[CH:23][C:19]=1[C:20]([OH:22])=[O:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Propane-1-sulfonyl chloride (0.0871 mL, 0.774 mmol) was dissolved in 10% Na2CO3 (1.65 mL, 1.55 mmol) at room temperature. 5-Amino-2-fluorobenzoic acid (0.100 g, 0.645 mmol) was added and heated to 60° C. overnight. Propane-1-sulfonyl chloride (0.0871 mL, 0.774 mmol) was added again, and the reaction mixture was heated at 60° C. for another hour. The reaction mixture was cooled to room temperature, diluted with water, taken to a pH of 10 with 10% Na2CO3 and extracted with DCM (2×). The reaction mixture was then taken to a pH of 2 with 1N HCl, extracted with DCM (3×) and concentrated to a solid, 2-fluoro-5-(propylsulfonamido)benzoic acid (29%).
Workup
- temperaturethe reaction mixture was heated at 60° C. for another hour
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with DCM (2×)
- extractionextracted with DCM (3×)
- concentrationconcentrated to a solid, 2-fluoro-5-(propylsulfonamido)benzoic acid (29%)
Sources & evidence
- ORD record
- ord-ebf10b2117744a0f93655657bfb9a213
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394795B2
Reaction notes
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