N-bromobutanimide → 5-bromo-1-tosyl-6,7-dihydro-1H-indazol-4(5H)-one

HRID 2366496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366496
[Br:1]N1C(=O)CCC1=O.[S:9]([N:19]1[C:27]2[CH2:26][CH2:25][CH2:24][C:23](=[O:28])[C:22]=2[CH:21]=[N:20]1)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][CH:24]1[CH2:25][CH2:26][C:27]2[N:19]([S:9]([C:12]3[CH:13]=[CH:14][C:15]([CH3:16])=[CH:17][CH:18]=3)(=[O:11])=[O:10])[N:20]=[CH:21][C:22]=2[C:23]1=[O:28]

Komponenten

5

Edukt 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 674585881-tosyl-6,7-dihydro-1H-indazol-4(5H)-one

Produkt 1

HCID 674593295-bromo-1-tosyl-6,7-dihydro-1H-indazol-4(5H)-oneAusbeute 70,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

According to Scheme 3 Step 3: N-Bromosuccinimide (3.44 mmol, 613 mg) was added to a solution of 1-tosyl-6,7-dihydro-1H-indazol-4(5H)-one (3.44 mmol, 1.00 g) in DCM (10 mL) and the reaction mixture was stirred at room temperature for 12 hours. A solution of NaHCO3 was added to the reaction mixture and the aqueous phase was extracted with DCM. The organic phase was dried over Na2SO4 and concentrated to yield 5-bromo-1-tosyl-6,7-dihydro-1H-indazol-4(5H)-one (2.44 mmol, 900 mg, 42%) as an orange oil.

Aufarbeitung

  1. extractionthe aqueous phase was extracted with DCM
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-34c1295e7aab4da987ee7bef4736974c
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697744B2

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