Methylamine → N-(2-chloro-5-thiazolylmethyl)-N'-methyl-N"-nitroguanidine

HRID 1276652Notes

Reaction equation

HRID 1276652 reaction equation
CO[C:3](=[N:12][N+:13]([O-:15])=[O:14])[NH:4][CH2:5][C:6]1[S:10][C:9]([Cl:11])=[N:8][CH:7]=1.[CH3:16][NH2:17]>O>[Cl:11][C:9]1[S:10][C:6]([CH2:5][NH:4][C:3]([NH:17][CH3:16])=[N:12][N+:13]([O-:15])=[O:14])=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea

Product 1

HCID 135779804N-(2-chloro-5-thiazolylmethyl)-N'-methyl-N"-nitroguanidineYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea (1.00 g, 4.00 mmol) in water (10 ml) was added 40% aqueous solution of methylamine (0.77 g, 9.92 mmol) dropwise. The mixture was stirred at room temperature for 14 hours and the resulting crystals were collected by filtration, washed with water (10 ml), and dried. As a result, 0.92 g (92.0% yield) of 1-(2-chloro-5-thiazolylmethyl)-3-methyl-2-nitroguanidine was obtained.

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. washwashed with water (10 ml)
  3. customdried

Sources & evidence

ORD record
ord-ef06d03365a44c23b8acf6ab8adcd952
Source dataset
uspto-grants-2000_12
Patent number
US06166215

Reaction notes

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