5-(Aminomethyl)-2-chloropyridine → HCID 178485038, compound

HRID 1769946Notes

Reaction equation

HRID 1769946 reaction equation
[C:1]([N:3]=[C:4](SC)[NH:5][CH3:6])#[N:2].[NH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[N:15][CH:16]=1>>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][NH:9][C:4](=[N:3][C:1]#[N:2])[NH:5][CH3:6])=[CH:16][N:15]=1

Participants

3

Reactant 2

HCID 70209275-(Aminomethyl)-2-chloropyridineHCID 178485082HCID 178485082, compound

Product 1

HCID 178485038HCID 178485038, compoundYield 44.4%

Conditions

Temperature
100 °C

Procedure

A mixture of 3-cyano-1-methyl-2-methylisothiourea (0.65 g) and 5-aminomethyl-2-chloropyridine (0.72 g) was stirred under heating at 100° C. for three hours. Then, the reaction product was cooled to room temperature and then purified on silica gel column chromatography (eluent: ethanol/chloroform) to obtain the desired 3-(2-chloro-5-pyridylmethyl)-1-methyl-2-cyanoguanidine (0.5 g) having a melting point in the range of from 193° to 197° C.

Workup

  1. temperatureThen, the reaction product was cooled to room temperature
  2. custompurified on silica gel column chromatography (eluent: ethanol/chloroform)

Sources & evidence

ORD record
ord-3bc4d0a6c3784fd7aeb378ee166a54fc
Source dataset
uspto-grants-1995_01
Patent number
US05384324

Reaction notes

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