Ethanol → N-[(E)-[3-[2-[4-(difluoromethoxy)phenyl]ethynyl]phenyl]methylideneamino]-4-methylbenzenesulfonamide

HRID 30552

Reaktionsgleichung

Reaktionsgleichung von HRID 30552
[F:1][CH:2]([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[CH:15]=O)=[CH:6][CH:5]=1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:31][NH2:32])(=[O:30])=[O:29])=[CH:24][CH:23]=1.CCO>O>[F:1][CH:2]([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14](/[CH:15]=[N:32]/[NH:31][S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:21])=[CH:23][CH:24]=3)(=[O:29])=[O:30])[CH:17]=[CH:18][CH:19]=2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 15303P-ToluenesulfonylhydrazideHCID 574358553-{[4-(Difluoromethoxy)phenyl]ethynyl}benzaldehyde

Produkt 1

HCID 59790336N-[(E)-[3-[2-[4-(difluoromethoxy)phenyl]ethynyl]phenyl]methylideneamino]-4-methylbenzenesulfonamideAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-{[4-(difluoromethoxy)phenyl]ethynyl}benzaldehyde (3.69 g, 13.57 mmol), 4-methylbenzenesulfonohydrazide (2.9 g, 15.6 mmol) and EtOH (11 mL) was refluxed for 30 minutes. cooled to room temperature, poured into water and extracted with ethyl ether. The organic extracts were combined dried over MgSO4 and concentrated in vacuo. The resultant residue was purified on silica gel (Biotage) using hexanes/EtOAc (2/1) as the eluting solvents to give N′-[(1E)-(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)methylene]-4-methylbenzenesulfonohydrazide as a tan solid (5.4 g, 90% yield), MS m/e (M+H)+ 441; 1H NMR (400 MHz, DMSO-d6) 2.32 (s, 3H), 7.2 (d, J=8.66 Hz, 2H), 7.3-7.6 (m, 8H), 7.72 (d, J=8.3 Hz, 2H), 7.88 (s, 1H), 11.54 (s, 1H).

Aufarbeitung

  1. temperaturewas refluxed for 30 minutes
  2. extractionextracted with ethyl ether
  3. dry with materialThe organic extracts were combined dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified on silica gel (Biotage)

Quellen und Nachweise

ORD-Eintrag
ord-e652b03b300e43f696c6c99f5bd0173e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

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