Sodium Chloride → O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea

HRID 613736Notes

Reaction equation

HRID 613736 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

5

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 183495401-(2-Chloro-1,3-thiazol-5-yl)methanamine--hydrogen chloride (1/1)HCID 136196430O-methyl-N-nitroisourea

Product 1

HCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisoureaYield 61.3%

Procedure

To an aqueous solution (31 ml) of sodium chloride (6.1 g, 0.10 mol) and O-methyl-N-nitroisourea (1.5 g, 12.9 mmol) was added 5-(aminomethyl)-2-chlorothiazole hydrochloride (2.4 g, 12.5 mmol). The reaction mixture was adjusted to pH 7.0 with aqueous sodium hydroxide solution, and stirred at room temperature for 4 hours. 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 1.92 g (60.8% 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-2b3fc69938aa4a5b916c2eb5ad94f537
Source dataset
uspto-grants-1999_12
Patent number
US06008363

Reaction notes

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