Hydrochloric Acid → 1-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine hydrochloride

HRID 77498

Reaktionsgleichung

Reaktionsgleichung von HRID 77498
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C.Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O.C(OCC)C.O1CCOCC1>[ClH:12].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[NH2:11])=[CH:15][CH:14]=1

Komponenten

10

Edukt 4

HCID 313Hydrochloric AcidHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 81531DiisopropylethylamineHCID 27239044-Methoxyphenylhydrazine hydrochloride

Produkt 1

HCID 189475691-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 4-Methoxyphenylhydrazine hydrochloride (10.0 g, 57.3 mmol), 4-chlorobenzylchloride (9.2 g, 57.2 mmol), tetrabutylammonium bromide (30.7 g, 11.5 mmol), and diisopropylethylamine (20 mL, 115 mmol) in CH2Cl2 (250 mL) was stirred at room temperature for several days. The reaction mixture was diluted with water and the organic layer was dried over MgSO4, filtered, and concentrated. The residue was taken up in toluene (200 mL) and diethyl ether (100 mL), and 1 equivalent of 4N HCl in dioxane was added at 0° C. The mixture was stirred at room temperature for 2 hours, and then evaporated to dryness to give the desired product (C-1; X═Cl) as a purple solid.

Aufarbeitung

  1. dry with materialthe organic layer was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-aa3a6fcfab7f4ae288aee51a9ed94b8b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841295B2

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