5-(Aminomethyl)-2-chloropyridine → 1-(6-Chloro-3-pyridylmethyl)-3-methyl2-nitroguanidine

HRID 1087103Notes

Reaction equation

HRID 1087103 reaction equation
[CH3:1][NH:2][C:3](=[N:6][N+:7]([O-:9])=[O:8])SC.[NH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[N:16][CH:17]=1>C(O)C>[Cl:18][C:15]1[N:16]=[CH:17][C:12]([CH2:11][NH:10][C:3]([NH:2][CH3:1])=[N:6][N+:7]([O-:9])=[O:8])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 70209275-(Aminomethyl)-2-chloropyridineHCID 1362270171,2-Dimethyl-3-nitroisothiourea

Product 1

HCID 1362181961-(6-Chloro-3-pyridylmethyl)-3-methyl2-nitroguanidineYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.45g of 1,2-dimethyl-3-nitroisothiourea, 0.43g of 5-(aminomethyl)-2-chloropyridine and 25ml of ethanol was refluxed for 6 hours and concentrated. The residue was purified by a column chromatography [developing solvent: chloroform-ethanol (5:1)] to afford 0.25g of 1-(6-chloro-3-pyridylmethyl)-3-methyl-2-nitroguanidine (Compound No. 5).

Workup

  1. temperaturewas refluxed for 6 hours
  2. concentrationconcentrated
  3. customThe residue was purified by a column chromatography [developing solvent: chloroform-ethanol (5:1)]

Sources & evidence

ORD record
ord-5a29a5580a9b4b6585d984440e5467d9
Source dataset
uspto-grants-1991_07
Patent number
US05034404

Reaction notes

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