6-Chloro-N-methyl-3-pyridinemethanamine → N-(2-chloropyrid-5-ylmethyl)-N-methyl-N'-nitroguanidine

HRID 1781592Notes

Reaction equation

HRID 1781592 reaction equation
CS[C:3](=[NH:8])[NH:4][N+:5]([O-:7])=[O:6].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH3:18])=[CH:12][N:11]=1>C(#N)C>[Cl:9][C:10]1[N:11]=[CH:12][C:13]([CH2:16][N:17]([CH3:18])[C:3]([NH2:8])=[N:4][N+:5]([O-:7])=[O:6])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 110948836-Chloro-N-methyl-3-pyridinemethanamineHCID 135927615N-Nitro-S-methylisothiourea

Product 1

HCID 53959606N-(2-chloropyrid-5-ylmethyl)-N-methyl-N'-nitroguanidineYield 31.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.676 g of S-methyl-N-nitroisothiourea, 0.783 g of 2-chloro-5-(methylaminomethyl)pyridine and 6 ml of acetonitrile was refluxed for 17 hours, and concentrated. The residue was recrystallized from ethanol to obtain 0.38 g of 1-(6-chloro-3-pyridylmethyl)-1-methyl-2-nitroguanidine (Compound No. 7).

Workup

  1. temperaturewas refluxed for 17 hours
  2. concentrationconcentrated
  3. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-eb6b1e439c704066992f2dc01030ffe1
Source dataset
uspto-grants-1997_05
Patent number
US05633375

Reaction notes

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