Tin tetrachloride dihydrate → 5-Amino-2-[2-(4-amino-phenyl)-vinyl]-benzenesulfonic Acid, 2,2-Dimethylpropyl Ester

HRID 277588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277588
[CH3:1][C:2]([CH3:29])([CH3:28])[CH2:3][O:4][S:5]([C:8]1[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:9]=1[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=1)(=[O:7])=[O:6].O.O.[Sn](Cl)(Cl)(Cl)Cl>C(OCC)(=O)C>[NH2:14][C:12]1[CH:11]=[CH:10][C:9]([CH:17]=[CH:18][C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=2)=[C:8]([S:5]([O:4][CH2:3][C:2]([CH3:29])([CH3:1])[CH3:28])(=[O:7])=[O:6])[CH:13]=1

Komponenten

4

Edukt 2

HCID 85782573Tin tetrachloride dihydrateHCID 867578655-Nitro-2-[2-(4-nitro-phenyl)-vinyl]-benzenesulfonic Acid 2,2-Dimethylpropyl Ester

Produkt 1

HCID 571227015-Amino-2-[2-(4-amino-phenyl)-vinyl]-benzenesulfonic Acid, 2,2-Dimethylpropyl EsterAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

5-Nitro-2-[2-(4-nitro-phenyl)-vinyl]-benzenesulfonic acid 2,2-dimethylpropyl ester (Example 56, 1.10 g, 2.62 mmol) was dissolved in 52 mL of ethyl acetate. Tin chloride dihydrate (2.95 g, 13.1 mmol) was added and a reflux condenser attached. The solution was heated to reflux and stirred overnight. After cooling to room temperature the solution was diluted with ethyl acetate (300 mL) and washed with saturated sodium bicarbonate. The whole mixture was filtered thru Celite and the aqueous layer discarded. The organic layer was then washed with brine and dried over MgSO4. After concentration on a rotovap the crude material was purified by a gradient flash column using 3 to 10% ethyl acetate in dichloromethane as the eluant to afford 0.33 g of the title compound as a oily red solid (35%): 1HNMR (CDCl3): δ7.63 (d, J=9 Hz, 1H), 7.58 (d, J=16 Hz, 1H), 7.33 (d, J=9 Hz, 2H), 7.31 (d, J=3 Hz, 1H), 6.89 (dd, J=9 Hz, 3 Hz, 1H), 6.86 (d, J=16 Hz, 1H), 6.68 (d, J=9 Hz, 2H), 3.89 (br s, 4H), 3.61 (s, 2H), 0.86 (s, 9H); MS (ES-POS): [M+H]+ 361; Analytical HPLC determined that this compound was 90% pure by C-18 reverse phase.

Aufarbeitung

  1. customa reflux condenser attached
  2. temperatureThe solution was heated
  3. temperatureto reflux
  4. washwashed with saturated sodium bicarbonate
  5. filtrationThe whole mixture was filtered thru Celite
  6. washThe organic layer was then washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationAfter concentration on a rotovap the crude material
  9. customwas purified by a gradient flash column

Quellen und Nachweise

ORD-Eintrag
ord-23a9b67d96e9418a95b9bf4493e5d40c
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355633B1

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