Ammonium Chloride → 3-(4-Dimethylaminomethyl-2-pyridylmethylthio)propionamidine hydrochloride

HRID 1382771Notes

Reaction equation

HRID 1382771 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][C:15](=[NH:18])OC)[CH:6]=1)[CH3:3].[Cl-:19].[NH4+:20]>C(O)C>[ClH:19].[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][C:15]([NH2:18])=[NH:20])[CH:6]=1)[CH3:3]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 19870407Methyl 3-(4-dimethylaminomethyl-2-pyridylmethylthio)propionimidate

Product 1

HCID 212733093-(4-Dimethylaminomethyl-2-pyridylmethylthio)propionamidine hydrochlorideYield 24.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-(4-dimethylaminomethyl-2-pyridylmethylthio)propionimidate (8.68 g), ammonium chloride (1.74 g) and ethanol (60 ml) were stirred at room temperature for 4 hours. Ethanol was evaporated at reduced pressure and the residue chromatographed using silica gel and a chloroform-methanol gradient elution. Fractions containing the required product (as shown by TLC) were combined and solvent evaporated at reduced pressure to give 3-(4-dimethylaminomethyl-2-pyridylmethylthio)propionamidine hydrochloride (2.30 g).

Workup

  1. customEthanol was evaporated at reduced pressure
  2. customthe residue chromatographed
  3. washa chloroform-methanol gradient elution
  4. additionFractions containing the required product (as shown by TLC)
  5. customsolvent evaporated at reduced pressure

Sources & evidence

ORD record
ord-3be3dee1014a486887f2e752899f2f8d
Source dataset
uspto-grants-1989_02
Patent number
US04808589

Reaction notes

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