4-Methylbenzaldehyde → 1-Hydroxy-N,N,4-Trimethyl-2-(4-Methylphenyl)-1H-Imidazole-5-Methanamine

HRID 224358

Reaktionsgleichung

Reaktionsgleichung von HRID 224358
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.Cl.[OH:11][N:12]=[C:13]([C:18](=O)[CH3:19])[CH2:14][N:15]([CH3:17])[CH3:16].[OH-].[NH4+:22]>CO>[OH:11][N:12]1[C:13]([CH2:14][N:15]([CH3:17])[CH3:16])=[C:18]([CH3:19])[N:22]=[C:6]1[C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 77254-MethylbenzaldehydeHCID 14923Ammonium HydroxideHCID 761752052-Hydroxyimino-1-Dimethylamino-3-Butanone Hydrochloride

Produkt 1

HCID 233329011-Hydroxy-N,N,4-Trimethyl-2-(4-Methylphenyl)-1H-Imidazole-5-Methanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-methylbenzaldehyde (12.6 g, 0.105 moles) in methanol (300 ml), ammonium hydroxide (sp. gr.=0.9, 180 ml) is added, followed by 2-hydroxyimino-1-dimethylamino-3-butanone hydrochloride (17.4 g, 0.0965 moles, described in Example 1). After standing overnight the mixture is evaporated to give a residue of the title compound. The residue is dissolved in methanol and a solution of hydrogen chloride in diethyl ether is added. The solution is treated with charcoal and filtered. The filtrate is evaporated and crystallized from methanol-diethyl ether to give the dihydrochloride salt of the title compound (23.99 g), mp 222°-224° C. Two recrystallizations from the latter solvent raised the melting point to 223°-226° C.; nmr (DMSO-d6) δ 2.4(s), 2.52(s), 2.83(s), 4.6(s), 7.35(s), 8.2(s) and 12.2(broad); and anal. Calc'd. for C14H19N3O.2HCl: C, 53.00; H, 6.62; N, 13.20% and Found: C, 52.55; H, 6.72; N, 13.34%.

Aufarbeitung

  1. customthe mixture is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-cb1cb14a18d54b218c38e84bb62d68f1
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04232029

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