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

HRID 613725Notes

Reaction equation

HRID 613725 reaction equation
CO[C:3](=[NH:8])[NH:4][N+:5]([O-:7])=[O:6].Cl.[Cl-].[Na+].[NH2:12][CH2:13][C:14]1[S:18][C:17]([Cl:19])=[N:16][CH:15]=1.[OH-].[Na+].[CH3:22]N>O>[Cl:19][C:17]1[S:18][C:14]([CH2:13][NH:12][C:3]([NH:8][CH3:22])=[N:4][N+:5]([O-:7])=[O:6])=[CH:15][N:16]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 6329MethylamineHCID 14798Sodium HydroxideHCID 101541292-Chloro-5-aminomethylthiazoleHCID 136196430O-methyl-N-nitroisourea

Product 1

HCID 135779804N-(2-chloro-5-thiazolylmethyl)-N'-methyl-N"-nitroguanidineYield 36.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of O-methyl-N-nitroisourea (2.0 g, 0.0168 mol), 36% hydrochloric acid (1.5 ml), sodium chloride (8.0 g), and water (40 ml) was added 5-aminomethyl-2-chlorothiazole (2.5 g, 0.0168 mol) at 20° C. This mixture was adjusted to pH 7 with 30% aqueous solution of sodium hydroxide and stirred at room temperature for 13 hours. Then, 40% aqueous solution of methylamine (4.4 ml, 0.0511 mol) was added and the mixture was stirred at room temperature for 2 hours. The resulting crystals were collected by filtration, washed with water, and dried to provide 1.54 g (36.7% yield) of 1-(2-chloro-5-thiazolylmethyl)-3-methyl-2-nitroguanidine.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. filtrationThe resulting crystals were collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-70f928931dc4452e9d6c4ff1e7e87f1d
Source dataset
uspto-grants-1999_12
Patent number
US06008363

Reaction notes

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