4-(4-chlorophenyl)-1H-imidazole-1,2-diamine → HCID 178478842, compound

HRID 357601Notes

Reaction equation

[OH:1][NH:2][C:3]([C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][C:9]2=[N:14]O)=[NH:4].N[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]>Cl>[ClH:28].[ClH:28].[OH:1][NH:2][C:3]([C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][C:9]2=[N:14][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]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1.026 g (5 mmol) of 4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-one oxime, 1.043 g (5 mmol) of 1,2-diamino-4-(4-chlorophenyl)-imidazole (see Beyer H. et al., Chem. Ber. 101, 3151 (1968)) and 20 ml of 4N hydrochloric acid is heated at 120° C. for 18 hours, with stirring, and is then concentrated by evaporation in vacuo. 25 ml of ethanol are added to the crystalline residue, the mixture is cooled to 5° C., with stirring, and is filtered, and the crystallizate is washed with a small amount of ethanol and diethyl ether. The crude title compound, dried under a high vacuum, contains 8.17% water and melts at 226°-228° C. (decomp.), 1H-NMR (D2O): δ=8.06 (d, 1H); 7.75 (d, 1H); 7.55 (t, 1H); 7.40 (s, 1H); 7.38 (d, 2H); 7.28 (d, 2H); 3.21-3.27 (m, 2H), 3.03-3.09 (m, 2H).

Workup

concentrationis then concentrated by evaporation in vacuo
addition25 ml of ethanol are added to the crystalline residue
temperaturethe mixture is cooled to 5° C.
stirringwith stirring
filtrationis filtered
washthe crystallizate is washed with a small amount of ethanol and diethyl ether
dry with materialThe crude title compound, dried under a high vacuum

Sources & evidence

ORD record: ord-b4174ecf0f224dc987eff26c6cb65c01
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840911

Reaction notes

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