Hydrochloric Acid → HCID 178478839, compound

HRID 357616Notes

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:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)[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:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)[N:20]=[C:19]1[NH2:33])=[NH:5]

Participants

Conditions

Temperature: 120 °C

Procedure

7 ml of concentrated hydrochloric acid are added, with stirring, to a mixture of 2.01 g (9.8 mmol) of 4-(N-hydroxyarnidino)-2,3-dihydro-1H-inden-1-one oxime, 2.2 g (9.8 mmol) of 1,2-diamino-4-(2-naphthyl)-imidazole (see J. Heterocycl. Chem. 11, 327-329 (1974)) and 25 ml of isopropanol, and the mixture is stirred at 120° C. for 24 hours. The mixture is cooled to 20° C., filtered and washed with isopropanol, and the filtration product is taken up in 60 ml of methylene chloride. The suspension is stirred at room temperature for 15 hours and is then filtered, and the crystallizate is washed with methylene chloride. In that manner there is obtained the title compound, m.p. 265°-270° C., 1H-NMR (DMSO/D2O): δ=8.32 (s, 1H); 8.29 (d, 1H); 8.19 (s, 1H); 8.04 (d, 1H); 7.88-7.98 (m, 3H); 7.81 (d, 1H); 7.53-7.68 (m, 3H); 3.38 (s, 4H).

Workup

temperatureThe mixture is cooled to 20° C.
filtrationfiltered
washwashed with isopropanol
stirringThe suspension is stirred at room temperature for 15 hours
filtrationis then filtered
washthe crystallizate is washed with methylene chloride

Sources & evidence

ORD record: ord-481e9830edae49fb880ceac58ce315b9
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840911

Reaction notes

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