HCID 178478845, compound → 1-[4-(Amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4,5-di-hydro-imidazole dihydrochloride

HRID 357611Notes

Reaction equation

HRID 357611 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[CH2:21][CH2:20][N:19]=[C:18]1[NH2:22])=[NH:6]>[Ni].O>[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[CH2:21][CH2:20][N:19]=[C:18]1[NH2:22])(=[NH:4])[NH2:6]

Participants

4

Reactant 1

HCID 178478845HCID 178478845, compound

Product 1

HCID 699043851-[4-(Amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4,5-di-hydro-imidazole dihydrochloride

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

Analogously to Example 2, approximately 2.0 g of Raney nickel are added to a solution of 4.75 g (0.0138 mol) of 1-[4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4,5-dihydro-imidazole dihydrochloride in 240 ml of water, and hydrogenation is carried out at room temperature and under normal pressure until the absorption of hydrogen has ceased. The reaction mixture is then filtered, adjusted to pH 4 with a small amount of 2N alcoholic hydrochloric acid and concentrated to dryness by evaporation. The residue is recrystallized from water, yielding the title compound in the form of the monohydrate, m.p. 280° C. (decomp.), 1H-NMR (DMSO/D2O): δ=8.17 (d, 1H); 7.66 (d, 1H); 7.54 (t, 1H); 4.18 (t, 2H); 3.70 (t, 2H); 3.25 (m, 2H); 3.13 (m, 2H).

Workup

  1. customis carried out at room temperature and under normal pressure until the absorption of hydrogen
  2. filtrationThe reaction mixture is then filtered
  3. concentrationconcentrated to dryness by evaporation
  4. customThe residue is recrystallized from water

Sources & evidence

ORD record
ord-3d0783ad72a14ddf96c3ca397da557a8
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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