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

HRID 357607Notes

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].Cl.N[N:19]1[CH:23]=[C:22]([CH2:24][CH3:25])[N:21]=[C:20]1[NH2:26]>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:19]1[CH:23]=[C:22]([CH2:24][CH3:25])[N:21]=[C:20]1[NH2:26])=[NH:5]

Participants

Conditions

Temperature: 80 °C

Procedure

3.2 ml of 32% hydrochloric acid (Merck, Darmstadt, Germany; p.a.) are added, with stirring, to a mixture of 3.28 g (0.016 mol) of 4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-one oxime, 2.6 g (0.016 mol) of 1,2-diamino-4-ethyl-imidazole hydrochloride and 150 ml of isopropanol, and the reaction mixture is stirred at 80° C. for 90 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. 245°-246° C., 1H-NMR (DMSO/D2O): δ=8.22 (d, 1H); 7.73 (d, 1H); 7.59 (t, 1H); 7.19 (s, 1H); 3.2 (m, 4H); 2.47 (m, 2H); 1.17 (t, 3H).

Workup

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

Sources & evidence

ORD record: ord-08a692f523fa4ed7bf73a2fba4d1c18c
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840911

Reaction notes

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