Hydrochloric Acid → HCID 178478840, compound

HRID 357612Notes

Reaction equation

HRID 357612 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]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[N:20]=[C:19]1[NH2:35]>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]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:27][CH:28]=2)[N:20]=[C:19]1[NH2:35])=[NH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9150354-(4-Phenylphenyl)imidazole-1,2-diamineHCID 178513250HCID 178513250, compound

Product 1

HCID 178478840HCID 178478840, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

20 ml of concentrated hydrochloric acid are added, with stirring, to a mixture of 5.09 g (0.0248 mol) of 4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-one oxime, 6.23 g (0.0248 mol) of 1,2-diamino-4-(4-biphenylyl)-imidazole and 70 ml of isopropanol, and the mixture is stirred at 120° C. for 28 hours. Cooling to room temperature, filtration, washing the crystallizate with isopropanol and drying under a high vacuum yield the title compound with a water content of 0.9%, m.p. 284°-285° C. (decomp.), 1H-NMR (DMSO/D2O): δ=8.28 (d, 1H); 7.99 (s, 4H); 7.80 (s, 4H); 7.60-7.76 (m, 4H); 7.35-7.53 (m, 3H); 3.32 (s, 4H).

Workup

  1. temperatureCooling to room temperature
  2. filtrationfiltration
  3. washwashing the crystallizate with isopropanol
  4. customdrying under a high vacuum

Sources & evidence

ORD record
ord-49201b4bfa3b450eb7297845e60a5674
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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