Water → 1-[4-(Amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-bi-phenylyl)-imidazole dihydrochloride

HRID 357615Notes

Reaction equation

HRID 357615 reaction equation
[ClH:1].Cl.O[NH:4][C:5]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][C:11]2=[N:16][N:17]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)[N:19]=[C:18]1[NH2:34])=[NH:6].O>[Ni].CO>[ClH:1].[ClH:1].[C:5]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][C:11]2=[N:16][N:17]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:24][CH:23]=2)[N:19]=[C:18]1[NH2:34])(=[NH:4])[NH2:6]

Participants

5

Reactant 2

HCID 962WaterHCID 178478840HCID 178478840, compound

Product 1

HCID 699046051-[4-(Amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-bi-phenylyl)-imidazole dihydrochloride

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Analogously to Example 2, a mixture of 9.27 g (18.54 mmol) of 1-[4-(N-hydroxy-amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-biphenylyl)-imidazole dihydrochloride, 800 ml of water, 820 ml of methanol and 7.3 g of Raney nickel is hydrogenated at 25°-51° C. and under normal pressure until the absorption of hydrogen has ceased. The reaction mixture is then filtered, the filtrate is acidified to pH 1 with concentrated hydrochloric acid, and concentration is carried out by evaporation in vacuo. Recrystallization of the residue twice from ethanol yields the title compound, m.p. 269°-270° C. (decomp.), 1H-NMR (DMSO/D2O): δ=8.32 (d, 1H); 8.03 (s, 1H); 7.62-7.83 (m, 8H); 7.35-7.53 (m, 3H); 3.36 (s, 4H).

Workup

  1. customis hydrogenated at 25°-51° C. and under normal pressure until the absorption of hydrogen
  2. filtrationThe reaction mixture is then filtered
  3. concentrationthe filtrate is acidified to pH 1 with concentrated hydrochloric acid, and concentration
  4. customis carried out by evaporation in vacuo
  5. customRecrystallization of the residue twice from ethanol

Sources & evidence

ORD record
ord-859b0ea4aa254339a5ff4ae575759d3e
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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