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

HRID 357591Notes

Reaction equation

HRID 357591 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]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[N:20]=[C:19]1[NH2:31]>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:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[N:20]=[C:19]1[NH2:31])=[NH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 124362921,2-Diamino-4-(4-methoxyphenyl)-imidazoleHCID 178513250HCID 178513250, compound

Product 1

HCID 1784887961-[4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-methoxyphenyl)-imidazole dihydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

7.2 ml of 32% hydrochloric acid (Merck, Darmstadt, Germany; p.a.) are added, with stirring, to a mixture of 4.92 g (0.024 mol) of 4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-one oxime, 4.9 g (0.024 mol) of 1,2-diamino-4-(4-methoxyphenyl)-imidazole (see Hetzheim A. et al., Chem. Ber. 100, 3418 (1967)) and 120 ml of isopropanol, and the reaction mixture is stirred at 80° C. for 19 hours. The reaction mixture is filtered while hot and the filtrate is cooled. The pale-yellow title product that has crystallised out is filtered off with suction and dried. It crystallizes in the form of the monohydrate, m.p. >220° C., MS (FAB): (M+H)+ =377, 1H-NMR (DMSO/D2O): δ=8.23 (d, 1H); 7.74 (s, 1H); 7.72 (d, 1H); 7.57-7.63 (m, 3H); 7.02 (d, 2H); 3.75 (s, 3H), 3.26 (s, 4H).

Workup

  1. filtrationThe reaction mixture is filtered while hot and the filtrate
  2. temperatureis cooled
  3. customThe pale-yellow title product that has crystallised out
  4. filtrationis filtered off with suction
  5. customdried
  6. customIt crystallizes in the form of the monohydrate, m.p. >220° C., MS (FAB)

Sources & evidence

ORD record
ord-9906ce6e4ba84fbbb26ca8d5d102d051
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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