Methylamine → 1-(6-Chloro-3-pyridylmethyl)-3-methyl2-nitroguanidine

HRID 613738Notes

Reaction equation

HRID 613738 reaction equation
CO[C:3](=[N:13][N+:14]([O-:16])=[O:15])[NH:4][CH2:5][C:6]1[CH:7]=[N:8][C:9]([Cl:12])=[CH:10][CH:11]=1.[CH3:17][NH2:18]>O>[Cl:12][C:9]1[N:8]=[CH:7][C:6]([CH2:5][NH:4][C:3]([NH:18][CH3:17])=[N:13][N+:14]([O-:16])=[O:15])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 136404633O-methyl-N-(6-chloro-3-pyridylmethyl)-N'-nitroisourea

Product 1

HCID 1362181961-(6-Chloro-3-pyridylmethyl)-3-methyl2-nitroguanidineYield 89.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of O-methyl-N-(6-chloro-3-pyridylmethyl)-N'-nitroisourea (970 mg, 3.96 mmol) and water (30 ml) was added 40% aqueous solution of methylamine (0.7 ml, 7.92 mmol, 2.0 equivalents) at room temperature with stirring. After 1.5 hours of stirring at room temperature, the resulting crystals were collected. The crystals were washed with water and methanol, and dried. As a result, 860 mg (89.1% yield) of 1-(6-chloro-3-pyridylmethyl)-3-methyl-2-nitroguanidine.

Workup

  1. stirringAfter 1.5 hours of stirring at room temperature
  2. customthe resulting crystals were collected
  3. washThe crystals were washed with water and methanol
  4. customdried

Sources & evidence

ORD record
ord-64525da0b4bf42b5b82636483c8b654c
Source dataset
uspto-grants-1999_12
Patent number
US06008363

Reaction notes

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