Bromomethyl 2-methoxyphenyl ketone → 2-Amino-1-benzylideneamino-4-(2-methoxyphenyl)-imidazole

HRID 357593

Reaktionsgleichung

Reaktionsgleichung von HRID 357593
[C:1]([NH:4][N:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[NH:3])[NH2:2].[CH3:13][O:14][C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=1[C:17](=O)[CH2:18]Br>C(O)C>[NH2:3][C:1]1[N:4]([N:5]=[CH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:18]=[C:17]([C:16]2[CH:21]=[CH:22][CH:23]=[CH:24][C:15]=2[O:14][CH3:13])[N:2]=1

Komponenten

4

Edukt 2

HCID 123440Bromomethyl 2-methoxyphenyl ketoneHCID 178513139HCID 178513139, Verbindung

Produkt 1

HCID 541454122-Amino-1-benzylideneamino-4-(2-methoxyphenyl)-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 41.7 g (0.257 mol) of benzaldehyde guanylhydrazone (see Thiele, A., Liebigs Annalen der Chemie 270, 35) and 30.12 g of 2-methoxyphenacyl bromide (Aldrich, Buchs, Switzerland; 98%, Cat. no. 10,085-4) in 130 ml of ethanol is boiled under reflux for one hour. After cooling, the product that has crystallised out is filtered off with suction and recrystallized from ethanol. In that manner there is obtained the title compound, m.p. 166°-167° C., 1H-NMR (DMSO): δ=8.61 (s, 1H); 8.0 (m, 3H); 7.88 (s, 1H); 7.5 (m, 3H); 7.19 (m, 1H); 7.03 (d, 1H); 6.96 (t, 1H); 6.16 (s, 2H); 3.94 (s, 3H).

Aufarbeitung

  1. temperatureunder reflux for one hour
  2. temperatureAfter cooling
  3. customthe product that has crystallised out
  4. filtrationis filtered off with suction
  5. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2f68083a6a144c5c80812bf0a9653c0c
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840911

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