Stannous chloride dihydrate → 2-(4'-Aminophenyl)-6-methylsulfoxy benzothiazole

HRID 1684831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1684831
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([O:20][S:21]([OH:24])(=[O:23])=[O:22])[C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([O:20][S:21]([OH:24])(=[O:23])=[O:22])[C:13]=3[N:14]=2)=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 672640042-(4'-Nitrophenyl)-6-methylsulfoxy benzothiazole

Produkt 1

HCID 672640372-(4'-Aminophenyl)-6-methylsulfoxy benzothiazoleAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-(4′-nitrophenyl)-6-methylsulfoxy benzothiazole (35 mg, 0.10 mmol) dissolved in ethanol (10 mL) was added SnCl2.2H2O (50 mg). The reaction mixture was heated to reflux for 1.5 hr. The solvent was then removed under reduced pressure. The residue was dissolved in ethyl acetate (10 mL), washed with 1N NaOH, water, dried over MgSO4. Evaporation of the solvent afforded 2-(4′-aminophenyl)-6-methylsulfoxy benzothiazole (21 mg, 65%) as pale brown solid. 1HNMR (300 MHz, CDCl3) δ (ppm): 8.02 (d, J=6.2 Hz, 1H), 7.92 (d, J=8.7 Hz, 2H), 7.84 (d, J=2.4 Hz, 1H), 7.38 (dd, J1=2.4 Hz, J2=6.2 Hz, 1H), 6.78 (d, J=8.7 Hz, 2H), 2.21 (s, 3H, CH3).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1.5 hr
  3. customThe solvent was then removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (10 mL)
  5. washwashed with 1N NaOH, water
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-7feeedf927c249cfbfd5096ba8896167
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08147798B2

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