1-[4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-tolyl)-imidazole dihydrochloride → 1-[4-(Amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-tolyl)-imidazole dihydrochloride

HRID 357604Notes

Reaction equation

HRID 357604 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]([CH3:28])=[CH:24][CH:23]=2)[N:19]=[C:18]1[NH2:29])=[NH:6]>[Ni].CO.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[CH:21]=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[N:19]=[C:18]1[NH2:29])(=[NH:4])[NH2:6]

Participants

4

Reactant 1

HCID 1784238931-[4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-tolyl)-imidazole dihydrochloride

Product 1

HCID 699031231-[4-(Amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-tolyl)-imidazole dihydrochloride

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

Analogously to Example 2, 0.2 g of Raney nickel is added to a solution of 0.9 g (1.917 mmol) of 1-[4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-tolyl)-imidazole dihydrochloride in 60 ml of methanol/water (1:1), 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, and the filtrate is acidified to pH 3 with 3N methanolic hydrochloric acid and is concentrated to a volume of approximately 20 ml. The product that has crystallized out is filtered off and recrystallized from ethanol/water, yielding the title compound with a water content of 11.81%, m.p. 220°-225° C. (decomp.), 1H-NMR (DMSO/D2O): δ=8.33 (d, 1H); 7.98 (s, 1H); 7.83 (d, 1H); 7.61-7.71 (m, 3H); 7.29 (d, 2H); 3.37 (s, 4H); 2.34 (s, 3H).

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. concentrationis concentrated to a volume of approximately 20 ml
  4. customThe product that has crystallized out
  5. filtrationis filtered off
  6. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-d21d31d3464e44c394eb321740764ef7
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

Loading…