Water → 1,2-Diamino-4-(2,5-dimethoxyphenyl)-imidazole

HRID 357597Notes

Reaction equation

HRID 357597 reaction equation
[NH2:1][C:2]1[N:3]([N:17]=CC2C=CC=CC=2)[CH:4]=[C:5]([C:7]2[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=2[O:15][CH3:16])[N:6]=1.O.NN.O>C(O)COCCO>[NH2:17][N:3]1[CH:4]=[C:5]([C:7]2[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=2[O:15][CH3:16])[N:6]=[C:2]1[NH2:1]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 539875062-Amino-1-benzylideneamino-4-(2,5-dimethoxyphenyl)-imidazole

Product 1

HCID 189379581,2-Diamino-4-(2,5-dimethoxyphenyl)-imidazole

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A solution of 26.1 g of 2-amino-1-benzylideneamino-4-(2,5-dimethoxyphenyl)-imidazole and 16.2 ml of hydrazine hydrate in 80 ml of diethylene glycol is stirred at 170° C. for 6 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 150 ml of ethanol. In that manner there is obtained the title compound, m.p. 159°-160° C., 1H-NMR (DMSO): δ=7.47 (d, 1H); 7.07 (s, 1H); 6.87 (d, 1H); 6.63 (q, 1H); 5.52 (s, 2H); 5.34 (s, 2H); 3.79 (s, 3H); 3.69 (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 150 ml of ethanol

Sources & evidence

ORD record
ord-4bb20e6c8400459cb80b82418e6c800f
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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