1,3-Benzodioxole-5-carboxaldehyde, 7-methoxy- → 2-[Hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-N-o-tolyl-benzenesulfonamide

HRID 1069483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1069483
[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9].C([Li])CCC.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]2[O:35][CH2:34][O:33][C:32]=12)[CH:28]=[O:29].[Cl-].[NH4+]>O1CCCC1>[OH:29][CH:28]([C:27]1[CH:26]=[C:25]([O:24][CH3:23])[C:32]2[O:33][CH2:34][O:35][C:31]=2[CH:30]=1)[C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:8]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:17])(=[O:9])=[O:10]

Komponenten

6

Edukt 4

HCID 220161,3-Benzodioxole-5-carboxaldehyde, 7-methoxy-HCID 25517Ammonium ChlorideHCID 87657Benzenesulfono-o-toluidideHCID 178418339Butyllithium

Produkt 1

HCID 186155802-[Hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-N-o-tolyl-benzenesulfonamideAusbeute 48,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-72 °C

Versuchsvorschrift

To tetrahydrofuran (200 mL) was added N-o-tolyl-benzenesulfonamide (4.95 g, 20 mmol). After cooling to −72° C., a solution of n-butyllithium (1.6 M, 25 mL in hexane) was added, and the mixture was stirred for 3 hours at −72° C. A solution of 3-methoxy-4,5-methylenedioxybenzaldehyde (3.60 g, 20 mmol) in tetrahydrofuran (70 mL) was added, and the mixture was stirred and warmed to 0° C. over 1.5 hours. The mixture was poured into 200-mL saturated ammonium chloride solution, and the organic phase was decanted. The solvent was evaporated in vacuo and the residue was suspended in ethyl ether, washed with saturated sodium bicarbonate and brine solutions. The solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to give a syrup which was chromatographed on 500 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65). The appropriate fractions were concentrated in vacuo and crystallized giving a solid, 4.15 g, 48.6% yield, mp 155-158° C. NMR spectra and elemental analysis were consistent with the structure.

Aufarbeitung

  1. stirringthe mixture was stirred
  2. temperaturewarmed to 0° C. over 1.5 hours
  3. customthe organic phase was decanted
  4. customThe solvent was evaporated in vacuo
  5. washwashed with saturated sodium bicarbonate and brine solutions
  6. dry with materialThe solution was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a syrup which
  10. customwas chromatographed on 500 g silica gel
  11. washeluted with a mixture of ethyl acetate and hexane (35:65)
  12. concentrationThe appropriate fractions were concentrated in vacuo
  13. customcrystallized
  14. customgiving a solid, 4.15 g, 48.6% yield, mp 155-158° C

Quellen und Nachweise

ORD-Eintrag
ord-02dddf334db14d83ae266163fc0a1e32
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06252070B1

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