Water → 1,2-Diamino-4-(2-methoxyphenyl)-imidazole

HRID 357594Notes

Reaction equation

HRID 357594 reaction equation
[NH2:1][C:2]1[N:3]([N:15]=CC2C=CC=CC=2)[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH3:14])[N:6]=1.O.NN.O>C(O)COCCO>[NH2:15][N:3]1[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH3:14])[N:6]=[C:2]1[NH2:1]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 541454122-Amino-1-benzylideneamino-4-(2-methoxyphenyl)-imidazole

Product 1

HCID 189379771,2-Diamino-4-(2-methoxyphenyl)-imidazole

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A solution of 23.2 g of 2-amino-1-benzylideneamino-4-(2-methoxyphenyl)-imidazole and 15.8 ml of hydrazine hydrate in 80 ml of diethylene glycol is stirred at 170° C. for 7 hours. After cooling, 400 ml of water are added to the reaction mixture. The product that has separated out is filtered off with suction, washed with water and recrystallized from 200 ml of ethanol. In that manner there is obtained the title compound, m.p. 195°-196° C., 1H-NMR (DMSO): δ=7.9 (d, 1H); 7.06 (m, 2H); 6.91 (m, 2H); 5.52 (s, 2H); 5.3 (s, 2H); 3.88 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. customThe product that has separated out
  3. filtrationis filtered off with suction
  4. washwashed with water
  5. customrecrystallized from 200 ml of ethanol

Sources & evidence

ORD record
ord-3d83890aab0e4bbda7baacfe12466996
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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