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

HRID 357593Notes

Reaction equation

HRID 357593 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: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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2f68083a6a144c5c80812bf0a9653c0c
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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