Iodine chloride → 4-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester

HRID 79029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79029
[C:1]([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]2[S:15][N:14]=[CH:13][C:12]=2[C:16]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([Si](C)(C)C)=[CH:20][C:19]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:29]Cl>C(Cl)Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>[C:1]([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]2[S:15][N:14]=[CH:13][C:12]=2[C:16]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:29])=[CH:20][C:19]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 24640Iodine chlorideHCID 670835784-(2-Fluoro-4-trimethylsilanyl-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester

Produkt 1

HCID 670836334-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl esterAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 24477Sodium ThiosulfateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution 4-(2-fluoro-4-trimethylsilanyl-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester (416 mg, 1.0 mmol) in DCM (10 mL) at −78° C. was added iodine monochloride as a solution in DCM (2.0 mL, 1M, 2.0 mmol). The reaction mixture was stirred at −78° C. for 1 hour then diluted with saturated aqueous sodium thiosulfate solution and extracted with DCM. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to yield the title compound as a yellow foam (459 mg, 98%). LCMS (Method B): RT=5.32 min, [M+H]+=471.

Aufarbeitung

  1. extractionextracted with DCM
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2ff70ac5481048b68eb181435c44d288
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841462B2

Notizen zur Reaktion

Wird geladen…