Hydrochloric Acid → 1-[4-(N-Hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(2,5-dimethoxyphenyl)-imidazole dihydrochloride

HRID 357595Notes

Reaction equation

HRID 357595 reaction equation
[ClH:1].[OH:2][NH:3][C:4]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][CH2:9][C:10]2=[N:15]O)=[NH:5].N[N:18]1[CH:22]=[C:21]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:24]=2[O:31][CH3:32])[N:20]=[C:19]1[NH2:33]>C(O)(C)C>[ClH:1].[ClH:1].[OH:2][NH:3][C:4]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][CH2:9][C:10]2=[N:15][N:18]1[CH:22]=[C:21]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:24]=2[O:31][CH3:32])[N:20]=[C:19]1[NH2:33])=[NH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 189379581,2-Diamino-4-(2,5-dimethoxyphenyl)-imidazoleHCID 178513250HCID 178513250, compound

Product 1

HCID 1784925651-[4-(N-Hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(2,5-dimethoxyphenyl)-imidazole dihydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

0.6 ml of concentrated hydrochloric acid is added, with stirring, to a mixture of 0.41 g (0.002 mol) of 4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-one oxime, 0.47 g (0.002 mol) of 1,2-diamino-4-(2,5-dimethoxyphenyl)-imidazole and 10 ml of isopropanol, and the reaction mixture is stirred at 80° C. for 3.hours. The reaction mixture is filtered while hot and the filtration product is washed with isopropanol and dried. In that manner there is obtained the title compound, m.p. >220° C., 1H-NMR (DMSO/D2 0): δ=8.23 (d, 1H); 7.75 (m, 2H); 7.61 (t, 1H); 7.17 (d, 1H); 7.07 (d, 1H); 6.93 (q, 1H); 3.82 (s, 3H), 3.71 (s, 3H); 3.25 (bs, 4H).

Workup

  1. filtrationThe reaction mixture is filtered while hot and the filtration product
  2. washis washed with isopropanol
  3. customdried

Sources & evidence

ORD record
ord-81b0d38fc8ca4f2ea604ea1041cf2e25
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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