Hydrochloric Acid → O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea

HRID 613730Notes

Reaction equation

HRID 613730 reaction equation
[Cl-].[Na+].[CH3:3][O:4][C:5](=[NH:10])[NH:6][N+:7]([O-:9])=[O:8].Cl.N[CH2:13][C:14]1[S:18][C:17]([Cl:19])=[N:16][CH:15]=1.[OH-].[Na+]>>[CH3:3][O:4][C:5](=[N:6][N+:7]([O-:9])=[O:8])[NH:10][CH2:13][C:14]1[S:18][C:17]([Cl:19])=[N:16][CH:15]=1

Participants

6

Reactant 5

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

Product 1

HCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisoureaYield 76.7%

Procedure

To an aqueous solution (40 ml) of sodium chloride (7.9 g, 0.13 mol) were added O-methyl-N-nitroisourea (2.3 g, 19.3 mmol), concentrated hydrochloric acid (1.49 ml, 16.8 mmol) and 5-(aminomethyl)-2-chlorothiazole (2.5 g, 16.8 mmol). The mixture was adjusted to pH 7.0 with 30% aqueous sodium hydroxide solution, and stirred at room temperature for 3 days. The resulting white crystals were collected by filtration under reduced pressure, and washed with water. The washed crystals were dried under reduced pressure (80° C., 2 hours) to provide 3.23 g (76.6% yield) of O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea.

Workup

  1. filtrationThe resulting white crystals were collected by filtration under reduced pressure
  2. washwashed with water
  3. customThe washed crystals were dried under reduced pressure (80° C., 2 hours)

Sources & evidence

ORD record
ord-15916411d7744832a0e8015366265d09
Source dataset
uspto-grants-1999_12
Patent number
US06008363

Reaction notes

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