Chlorosuccinimide → 2-(4-Tert-butyl-benzenesulfonylamino)-5-chloro-4-fluoro-benzoic acid
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:25]N1C(=O)CCC1=O>C(O)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[CH:23]=[C:22]([F:24])[C:21]([Cl:25])=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]Participants
Conditions
- Temperature
- 80 °C
Procedure
2-(4-tert-Butyl-benzenesulfonylamino)-4-fluoro-benzoic acid (23 g, 65.5 mmol) was added to 230 mL of stirring acetic acid in a 500 mL round bottom flask. N-chlorosuccinimide (17.5 g, 131 mmol) was then added and the mixture heated to 80° C. under a N2 atmosphere. The reaction was determined to be complete in seven hours according to LCMS analysis. The heat bath was subsequently removed and the reaction was quenched via the addition of 250 mL of a 50% solution of sodium metabisulfite. The mixture immediately formed a thick white slurry which was allowed to stir for approximately 15 minutes. Vacuum filtration of the slurry resulted in a white solid that was washed with a small amount of water and dried in vacuo to generate 22 g of 2-(4-tert-butyl-benzenesulfonylamino)-5-chloro-4-fluoro-benzoic acid (white solid, 87% yield): HPLC retention time=2.87 minutes; MS (ES) M+H expected 386.0, found 386.0.
Workup
- customThe heat bath was subsequently removed
- customthe reaction was quenched via the addition of 250 mL of a 50% solution of sodium metabisulfite
- customThe mixture immediately formed a thick white slurry which
- filtrationVacuum filtration of the slurry
- customresulted in a white solid
- washthat was washed with a small amount of water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-310724464a844f7ebde8f04ce2fd3d47
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07718683B2
Reaction notes
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