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

HRID 1276653Notes

Reaction equation

HRID 1276653 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].Cl>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea

Product 1

HCID 135779804N-(2-chloro-5-thiazolylmethyl)-N'-methyl-N"-nitroguanidineYield 95.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea (87% purity, 47.2 g, 0.164 mol) in water (410 ml) was added 40% aqueous solution of methylamine (25.5 g, 0.328 mol, 2.0 equivalents) dropwise at 23° C. After 2 hours of stirring at room temperature, the mixture was allowed to stand under ice-cooling and then, 36% hydrochloric acid (14.3 mol, 0.168 mol) was added dropwise at 13-20° C. The resulting crystals were collected by filtration to provide 39.1 g (95.6% yield) of 1-(2-chloro-5-thiazolylmethyl)-3-methyl-2-nitroguanidine.

Workup

  1. temperaturecooling
  2. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-29492e36647741598e296f56877b6aa6
Source dataset
uspto-grants-2000_12
Patent number
US06166215

Reaction notes

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