Acetonitrile → 4-(4-Phenylphenyl)imidazole-1,2-diamine

HRID 357614Notes

Reaction equation

HRID 357614 reaction equation
[NH2:1][C:2]1[N:3]([N:19]=CC2C=CC=CC=2)[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[N:6]=1.O.NN.C(#N)C>C(O)COCCO>[NH2:19][N:3]1[CH:4]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][CH:12]=2)[N:6]=[C:2]1[NH2:1]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24654Hydrazine hydrate (1:1)HCID 39800002-Amino-1-benzylideneamino-4-(4-biphenylyl)-imidazole

Product 1

HCID 9150354-(4-Phenylphenyl)imidazole-1,2-diamine

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 9.2 g (0.0189 mol) of 2-amino-1-benzylideneamino-4-(4-biphenylyl)-imidazole and 22 ml of hydrazine hydrate in 73 ml of diethylene glycol is stirred at 140° C. for 48 hours. After cooling to 20° C., 100 ml of acetonitrile are added to the reaction mixture, which is then cooled further to 5° C. The product that has separated out is filtered off and washed with acetonitrile and diethyl ether. In that manner there is obtained the title compound having a water content of 0.41 %, m.p. >280° C., 1H-NMR (DMSO): δ=7.29-7.73 (m, 9H); 7.12 (s, 1H); 5.55 (s, 2H); 5.39 (s, 2H).

Workup

  1. temperatureis then cooled further to 5° C
  2. customThe product that has separated out
  3. filtrationis filtered off
  4. washwashed with acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-e7fa5f72c3074203b8911dfac0b85803
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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