Bromomethyl 3-methoxyphenyl ketone → 2-Amino-1-benzylideneamino-4-(3-methoxyphenyl)-imidazole

HRID 357599Notes

Reaction equation

HRID 357599 reaction equation
[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:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18](=O)[CH2:19]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:19]=[C:18]([C:17]2[CH:22]=[CH:23][CH:24]=[C:15]([O:14][CH3:13])[CH:16]=2)[N:2]=1

Participants

4

Reactant 2

HCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 178513139HCID 178513139, compound

Product 1

HCID 540477532-Amino-1-benzylideneamino-4-(3-methoxyphenyl)-imidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 16.2 g (0.1 mol) of benzaldehyde guanylhydrazone and 11.8 g (0.050 mol) of 3-methoxyphenacyl bromide (Aldrich, Buchs, Switzerland; 98 %, Cat. no. 11,567-3) in 50 ml of ethanol is stirred at 20° C. for 3 hours. The product that has crystallized out is filtered off with suction and dried. In that manner there is obtained the title compound, m.p. 170°-171° C., 1H-NMR (DMSO): δ=8.56 (s, 1H); 8.03 (s, 1H); 7.92 (m, 2H); 7.5 (m, 3H); 7.26 (m, 3H); 6.76 (m, 1H); 6.2 (s, 2H); 3.8 (s, 3H).

Workup

  1. customThe product that has crystallized out
  2. filtrationis filtered off with suction
  3. customdried

Sources & evidence

ORD record
ord-a4af0387c5784795ac984847918570e8
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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