Sulfamide → 1-(2-Fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

HRID 1818771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1818771
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=1.[S:16](N)(N)(=[O:18])=[O:17]>COCCOCCOC.CCOCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][S:16]1(=[O:18])=[O:17]

Komponenten

5

Edukt 2

HCID 82267SulfamideHCID 19039441N1-(2-Fluorophenyl)benzene-1,2-diamine

Produkt 1

HCID 468330941-(2-Fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxideAusbeute 23,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8150DiglymeLösungsmittel2×

Versuchsvorschrift

Dry diglyme (10 mL) was added to a flask equipped with a dropping funnel under a nitrogen atmosphere and brought to a vigorous reflux N-(2-fluorophenyl)benzene-1,2-diamine (1.2 g, 6.0 mmol) and sulfamide (0.69 g, 7.2 mmol) were dissolved in 5 mL of diglyme and placed in the dropping funnel. The mixture was added dropwise to the flask over 15 minutes and then refluxing was continued for an additional 15 minutes. The mixture was cooled to ambient temperature and diluted with ether, washed with water, 2N HCl, water, brine, dried over anhydrous magnesium sulfate, and concentrated. The crude product was purified via Isco chromatography (Redisep, silica, gradient 5-50% (ethyl acetate containing 2% formic acid) in hexane) to afford 1-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (0.37 g).

Aufarbeitung

  1. customequipped with a dropping funnel under a nitrogen atmosphere
  2. additionThe mixture was added dropwise to the flask over 15 minutes
  3. temperaturerefluxing
  4. washwashed with water, 2N HCl, water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified via Isco chromatography (Redisep, silica, gradient 5-50% (ethyl acetate containing 2% formic acid) in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-74c91b520f1d4741a148da04c0ec3175
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601722B2

Notizen zur Reaktion

Wird geladen…