Hydrochloric Acid → HCID 178422462, compound

HRID 1493332Notes

Reaction equation

HRID 1493332 reaction equation
C([NH:9][C:10]([NH:24][CH2:25][CH2:26][CH2:27][C:28]1[N:29]=[CH:30][NH:31][CH:32]=1)=[N:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([Br:23])=[CH:18][N:17]=1)(=O)C1C=CC=CC=1.C[O-].[Na+].[ClH:36]>>[ClH:36].[ClH:36].[ClH:36].[Br:23][C:19]1[CH:20]=[C:21]([CH3:22])[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:10]([NH2:9])=[N:24][CH2:25][CH2:26][CH2:27][C:28]2[N:29]=[CH:30][NH:31][CH:32]=2)=[N:17][CH:18]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 178422461HCID 178422461, compound

Product 1

HCID 178422462HCID 178422462, compoundYield 60%

Procedure

1.00 g (2 mmol) of N1 -Benzoyl-N2 -[4-(5-bromo-3-methyl-pyridin-2-yl)butyl]-N3 -[3-(1H-imidazol-4-yl) propyl]-guanidine is boiled in 20 ml of conc. hydrochloric acid for 18 hours. The aqueous solution diluted to 40 ml after cooling is extracted with 4×20 ml of diethylether, filtered and concentrated by evaporation under vacuum. The residue is taken up twice with 20 ml of absolute ethanol and concentrated by evaporation. The crude product obtained is then converted into the base with sodium methylate and chromatographed on aluminium oxide with ethyl acetate/ methanol (1:1). After concentration by evaporation, the main fraction is taken up with 5 ml of water, 0.5 ml of conc.hydrochloric acid is added, and the mixture is concentrated by evaporation under vacuum. After the mixture has again been concentrated by evaporation with 20 ml of absolute ethanol, 0.62 g (60%) of the title compound is obtained, in the form of a colourless, hygroscopic solid.

Workup

  1. additionThe aqueous solution diluted to 40 ml
  2. temperatureafter cooling
  3. extractionis extracted with 4×20 ml of diethylether
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation under vacuum
  6. concentrationconcentrated by evaporation
  7. customThe crude product obtained
  8. customchromatographed on aluminium oxide with ethyl acetate/ methanol (1:1)
  9. concentrationAfter concentration
  10. customby evaporation
  11. additionhydrochloric acid is added
  12. concentrationthe mixture is concentrated by evaporation under vacuum
  13. concentrationAfter the mixture has again been concentrated by evaporation with 20 ml of absolute ethanol

Sources & evidence

ORD record
ord-8e40eae84cdf46d8890f8d11252e8ced
Source dataset
uspto-grants-1991_06
Patent number
US05021431

Reaction notes

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