Ethanol → Ethyl (7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)acetate

Reaktionsgleichung

OS(O)(=O)=O.[OH:6][C:7]1[CH:22]=[CH:21][C:10]2[NH:11][C:12]([CH2:17][C:18]([OH:20])=[O:19])=[N:13][S:14](=[O:16])(=[O:15])[C:9]=2[CH:8]=1.[CH3:23][CH2:24]O>>[CH2:23]([O:19][C:18](=[O:20])[CH2:17][C:12]1[NH:11][C:10]2[CH:21]=[CH:22][C:7]([OH:6])=[CH:8][C:9]=2[S:14](=[O:16])(=[O:15])[N:13]=1)[CH3:24]

Komponenten

Edukt 3

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 11368865(7-Hydroxy-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid

Produkt 1

HCID 46942308Ethyl (7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)acetate

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

EtOH (15 mL) and 150 μL of H2SO4 (conc.) were added into the compound 10c (5.03 mmol) and the mixture was heated to 80° C. for 45 minutes with stirring. The solvent was partially evaporated to half of the original volume under reduced pressure. EtOAc (30 mL) was added and the resulted mixture was washed with H2O (15 mL×3) via extraction. The aqueous layer was back extracted with EtOAc once (60 mL) and the combined organic layer was dried over anhydrous MgSO4, filtered, concentrated to give the desired product (4b) (1.11 g) as a gray solid. This crude material was directly used in next step without further purification. LC-MS: (ESI+) m/e=285.10 [M+1]+ (exact ms: 284.05).

Aufarbeitung

customThe solvent was partially evaporated to half of the original volume under reduced pressure
additionEtOAc (30 mL) was added
washthe resulted mixture was washed with H2O (15 mL×3) via extraction
extractionThe aqueous layer was back extracted with EtOAc once (60 mL)
dry with materialthe combined organic layer was dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-c173e85b08924514b3c9533037c98213
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07425552B2

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