HCID 178478842, compound → 1-[4-(Amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-chlorophenyl)-imidazole dihydrochloride

HRID 357602Notes

Reaction equation

HRID 357602 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]([Cl:28])=[CH:24][CH:23]=2)[N:19]=[C:18]1[NH2:29])=[NH:6]>[Ni].CO.O>[ClH:28].[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]([Cl:28])=[CH:26][CH:27]=2)[N:19]=[C:18]1[NH2:29])(=[NH:4])[NH2:6]

Participants

5

Reactant 1

HCID 178478842HCID 178478842, compound

Product 1

HCID 699047171-[4-(Amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-chlorophenyl)-imidazole dihydrochloride

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Analogously to Example 2, 0.2 g of Raney nickel is added to a solution of 1.0 g (2.024 mmol) of 1-[4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-chlorophenyl)-irnidazole dihydrochloride in 35 ml of methanol and 20 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 diluted with 50 ml of methanol and filtered. The filtrate is adjusted to pH 3 with a small amount of 3N methanolic hydrochloric acid and is concentrated to a volume of approximately 30 ml. After cooling in an ice-bath, the product that has crystallized out is filtered off, washed with a small amount of methanol and diethyl ether and dried under a high vacuum at 120° C. The title compound is obtained in the form of the monohydrate, m.p. 245°-250° C. (decomp.), 1H-NMR (DMSO/D2O): δ=8.33 (d, 1H); 8.12 (s, 1H); 7.79-7.87 (m, 3H); 7.67 (t, 1H); 7.57 (d, 2H); 3.38 (s, 4H).

Workup

  1. customis carried out at room temperature and under normal pressure until the absorption of hydrogen
  2. additionThe reaction mixture is then diluted with 50 ml of methanol
  3. filtrationfiltered
  4. concentrationis concentrated to a volume of approximately 30 ml
  5. temperatureAfter cooling in an ice-bath
  6. customthe product that has crystallized out
  7. filtrationis filtered off
  8. washwashed with a small amount of methanol and diethyl ether
  9. customdried under a high vacuum at 120° C

Sources & evidence

ORD record
ord-d0c0d795eb934f6383a31881b74b848e
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

Loading…