Hydrochloric Acid → HCID 178449214, compound

HRID 1165912Notes

Reaction equation

HRID 1165912 reaction equation
C([NH:9][C:10]([NH:20][CH2:21][CH2:22][C:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:24])=[N:11][CH2:12][CH2:13][CH2:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1)(=O)C1C=CC=CC=1.[ClH:37]>>[ClH:37].[NH:18]1[CH:19]=[C:15]([CH2:14][CH2:13][CH2:12][NH:11][C:10]([NH2:9])=[N:20][CH2:21][CH2:22][C:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:24])[N:16]=[CH:17]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 178449180HCID 178449180, compound

Product 1

HCID 178449214HCID 178449214, compound

Procedure

1.00 g (2.1 mmol) of N1 -benzoyl-N2 -[3-(1H-imidazol-4-yl) propyl]-N3 -(3,3-diphenylbutyl)-guanidine are boiled under reflux with 20 ml of conc. hydrochloric acid for 20 hours. After the reaction mixture has been highly concentrated by evaporation under vacuum, the residue is diluted with 30 ml of water. The solution is extracted 5 times with 20 ml portions of diethylether. The aqueous phase is then filtered and concentrated by evaporation under vacuum at temperatures of up to 50° C. and the residue is concentrated twice by evaporation with 10 ml portions of absolute ethanol. The crude product obtained is chromatographed on silica gel with dichloromethane/methanol (80:20) as solvent. After concentration by evaporation under vacuum, the main fraction yields 0.53 g (61%) of a colourless, amorphous solid.

Workup

  1. concentrationAfter the reaction mixture has been highly concentrated by evaporation under vacuum
  2. additionthe residue is diluted with 30 ml of water
  3. extractionThe solution is extracted 5 times with 20 ml portions of diethylether
  4. filtrationThe aqueous phase is then filtered
  5. concentrationconcentrated by evaporation under vacuum at temperatures of up to 50° C.
  6. concentrationthe residue is concentrated twice by evaporation with 10 ml portions of absolute ethanol

Sources & evidence

ORD record
ord-fbc09b3f958c4c148c123cc7325b79a9
Source dataset
uspto-grants-1990_03
Patent number
US04912119

Reaction notes

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