Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[Cl:12][S:13](O)(=[O:15])=[O:14]>C(Cl)Cl>[F:1][C:2]1[C:3]([S:13]([Cl:12])(=[O:15])=[O:14])=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
According to Scheme 11, a mixture of commercially-available 5-fluoro-1,3-benzoxazol-2(3H)-one (11-1, 1.02 g, 6.66 mmol) in DCM (66.6 ml) at RT was added chlorosulfonic acid (4.46 ml, 66.6 mmol). The suspension gradually became a solution and was stirred for 18 h at RT. Following this duration, LCMS showed complete consumption of starting material. The solution was cooled to 0° C. and carefully quenched with ice chips and then partitioned between water (100 mL) and EtOAc (100 mL). The layers were separated and the aqueous layer was back-extracted with 3×20 mL DCM and 2×20 mL EtOAc. The combined organic layers were washed with saturated aqueous NaHCO3 (30 mL), dried over sodium sulfate and filtered. Concentration in vacuo to yield 11-2 (5-Fluoro-2-oxo-2,3-dihydro-1,3-benzoxazole-6-sulfonyl chloride) as a tan solid, which was used without purification.
Workup
- customconsumption of starting material
- temperatureThe solution was cooled to 0° C.
- customcarefully quenched with ice chips
- custompartitioned between water (100 mL) and EtOAc (100 mL)
- customThe layers were separated
- extractionthe aqueous layer was back-extracted with 3×20 mL DCM and 2×20 mL EtOAc
- washThe combined organic layers were washed with saturated aqueous NaHCO3 (30 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationConcentration in vacuo
Sources & evidence
- ORD record
- ord-272cfea00f6f45118157f9f20ec9a6d7
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273040B2
Linked notes
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