Chlorosulfonic acid → 5-Fluoro-2-oxo-2,3-dihydro-1,3-benzoxazole-6-sulfonyl chloride

HRID 920225

Reaktionsgleichung

Reaktionsgleichung von HRID 920225
[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]=1

Komponenten

4

Edukt 2

HCID 24638Chlorosulfonic acidHCID 2872085-Fluoro-2(3H)-benzoxazolone

Produkt 1

HCID 822761655-Fluoro-2-oxo-2,3-dihydro-1,3-benzoxazole-6-sulfonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customconsumption of starting material
  2. temperatureThe solution was cooled to 0° C.
  3. customcarefully quenched with ice chips
  4. custompartitioned between water (100 mL) and EtOAc (100 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was back-extracted with 3×20 mL DCM and 2×20 mL EtOAc
  7. washThe combined organic layers were washed with saturated aqueous NaHCO3 (30 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationConcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-272cfea00f6f45118157f9f20ec9a6d7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273040B2

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