Ethyl 2-(4-chloro-1-hydroxy-6-(5-nitro-1,3,4-thiadiazol-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetate → Ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-4-chloro-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetate

HRID 1798304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798304
[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([O:18][C:19]2[S:20][C:21]([N+:24]([O-])=O)=[N:22][N:23]=2)[CH:3]=1>CCO.O.Cl>[NH2:24][C:21]1[S:20][C:19]([O:18][C:4]2[CH:3]=[C:2]([Cl:1])[C:10]3[CH:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][B:7]([OH:17])[C:6]=3[CH:5]=2)=[N:23][N:22]=1

Komponenten

5

Edukt 1

HCID 58292595Ethyl 2-(4-chloro-1-hydroxy-6-(5-nitro-1,3,4-thiadiazol-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetate

Produkt 1

HCID 58292780Ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-4-chloro-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetateAusbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-(4-chloro-1-hydroxy-6-(5-nitro-1,3,4-thiadiazol-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetate (430 mg, 1.08 mmol) in EtOH (15 mL) and H2O (5 mL) was added 2 drops of conc. HCl and the mixture was heated to reflex for 2 h. Upon cooling, the reaction mixture was filtered and the EtOH was removed under the reduced pressure and the residue was extracted with EtOAc (3×10 ml). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to give the crude product as a yellow oil (330 mg). MS (ESI) m/z=370 [M+H]+.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureUpon cooling
  3. filtrationthe reaction mixture was filtered
  4. customthe EtOH was removed under the reduced pressure
  5. extractionthe residue was extracted with EtOAc (3×10 ml)
  6. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3b41c1d75ef24e2eab5bec8274e55353
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

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