1-Chloro-4-(chloromethyl)benzene → 1-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine

HRID 1609218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1609218
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.C(NC(C)C)(C)C.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[NH2:11])=[CH:22][CH:21]=1

Komponenten

6

Edukt 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 7912DiisopropylamineHCID 27239044-Methoxyphenylhydrazine hydrochloride

Produkt 1

HCID 149805641-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension under N2 of 4-methoxyphenylhydrazine hydrochloride (41 g, 230 mmol) in methylene chloride (1000 ml) were added diisopropylamine (79.8 g, 612 mmol), 4-chlorobenzyl chloride (40.25 g, 250 mmol) and tetrabutylammonium bromide (22.8 g, 70 mmol), and the resulting mixture was stirred at room temperature for 48 hours. The reaction mixture was then washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (2.5% methanol/methylene chloride), followed by washing of the solid with 10% ethyl ether in hexane and drying in vacuo to provide 43.5 g of 1-(4-chlorobenzyl)-1-(4-methoxyphenyl)hydrazine. mp.55° C.

Aufarbeitung

  1. washThe reaction mixture was then washed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (2.5% methanol/methylene chloride)
  6. washby washing of the solid with 10% ethyl ether in hexane
  7. customdrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-033cb681b4324a7a82dfee28727d1660
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05399699

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