Hydrochloric Acid → HCID 178433686, compound

HRID 354527Notes

Reaction equation

HRID 354527 reaction equation
C([NH:9][C:10]([NH:22][CH2:23][CH2:24][CH2:25][C:26]1[N:27]=[CH:28][NH:29][CH:30]=1)=[N:11][CH2:12][CH2:13][S:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][C:20]=1[CH3:21])(=O)C1C=CC=CC=1.[ClH:31]>>[ClH:31].[ClH:31].[ClH:31].[NH:29]1[CH:30]=[C:26]([CH2:25][CH2:24][CH2:23][NH:22][C:10]([NH:11][CH2:12][CH2:13][S:14][CH2:15][C:16]2[N:17]=[CH:18][NH:19][C:20]=2[CH3:21])=[NH:9])[N:27]=[CH:28]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 178433678HCID 178433678, compound

Product 1

HCID 178433686HCID 178433686, compound

Procedure

N-Benzoyl-N'-[3-(4-imidazolyl)propyl]-N"-[2-(5-methyl-4-imidazolylmethylthio)ethyl]guanidine (2.37 g) was heated overnight on a steam bath with conc. hydrochloric acid (135 ml). The aqueous reaction mixture was evaporated to ca 75% of its original volume to remove the excess of hydrogen chloride. The aqueous residue obtained was extracted with diethyl ether to remove benzoic acid. The aqueous phase was evaporated at reduced pressure and azeotroped with ethanol (100 ml). The oily residue was recrystallised from ethanol to yield N-[3-(4-imidazolyl)propyl]-N'-[2-(5-methyl-4-imidazolylmethylthio)ethyl]guanidine trihydrochloride (1.93 g) m.p. 200°-201° C.

Workup

  1. customThe aqueous reaction mixture was evaporated to ca 75% of its original volume
  2. customto remove the excess of hydrogen chloride
  3. customThe aqueous residue obtained
  4. extractionwas extracted with diethyl ether
  5. customto remove benzoic acid
  6. customThe aqueous phase was evaporated at reduced pressure
  7. customazeotroped with ethanol (100 ml)
  8. customThe oily residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-6807e3b3291b4d76907d0f0f31a978d6
Source dataset
uspto-grants-1983_03
Patent number
US04375435

Reaction notes

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