Hydrochloric Acid → O-methyl-N-(6-chloro-3-pyridylmethyl)-N'-nitroisourea

HRID 613737Notes

Reaction equation

HRID 613737 reaction equation
[CH3:1][O:2][C:3](=[NH:8])[NH:4][N+:5]([O-:7])=[O:6].Cl.N[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[N:16][CH:17]=1.[OH-].[Na+]>O>[CH3:1][O:2][C:3](=[N:4][N+:5]([O-:7])=[O:6])[NH:8][CH2:11][C:12]1[CH:17]=[N:16][C:15]([Cl:18])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70209275-(Aminomethyl)-2-chloropyridineHCID 136196430O-methyl-N-nitroisourea

Product 1

HCID 136404633O-methyl-N-(6-chloro-3-pyridylmethyl)-N'-nitroisoureaYield 47.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of O-methyl-N-nitroisourea (1.25 g, 10.53 mmol), water (20 ml) and concentrated hydrochloric acid (0.85 ml, 10.03 mmol) was added 5-(aminomethyl)-2-chloropyridine (1.43 g, 10.03 mmol) dropwise over 5 minutes at room temperature with stirring. The reaction mixture was neutralized with 40% aqueous sodium hydroxide solution and adjusted to pH 7.2. After 17 hours of stirring at room temperature, the resulting crystals were collected. The crystals were washed with water and dried. As a result, 1.16 g (47.3% yield) of O-methyl-N-(6-chloro-3-pyridylmethyl)-N'-nitroisourea was obtained as white crystals. M.p. 112-113° C.

Workup

  1. stirringAfter 17 hours of stirring at room temperature
  2. customthe resulting crystals were collected
  3. washThe crystals were washed with water
  4. customdried

Sources & evidence

ORD record
ord-77edc11a8908401eab15bb05bace7992
Source dataset
uspto-grants-1999_12
Patent number
US06008363

Reaction notes

Loading…