Hydrogen Bromide → O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea

HRID 1276659Notes

Reaction equation

HRID 1276659 reaction equation
[NH2:1][CH2:2][C:3]1[S:7][C:6]([Cl:8])=[N:5][CH:4]=1.Br.[CH3:10][O:11][C:12](=N)[NH:13][N+:14]([O-:16])=[O:15].[Cl-].[Na+].[OH-].[Na+]>O>[CH3:10][O:11][C:12](=[N:13][N+:14]([O-:16])=[O:15])[NH:1][CH2:2][C:3]1[S:7][C:6]([Cl:8])=[N:5][CH:4]=1

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 101541292-Chloro-5-aminomethylthiazoleHCID 136196430O-methyl-N-nitroisourea

Product 1

HCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisoureaYield 69.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(Aminomethyl)-2-chlorothiazole (7.43 g, 50.0 mmol) was dissolved in water (96 ml), and 47% hydrobromic acid (5.78 ml 50.0 mmol) was added. The pH was 3.4 at this time. To this reaction mixture was added O-methyl-N-nitroisourea. (7.19 g, 60.0 mmol) and sodium chloride (17.5 g, 0.30 mol), and adjusted to pH 6.2 with aqueous sodium hydroxide solution (0.5 N) using pH meter. After 24 hours of stirring at room temperature, 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 8.7 g (69.4% 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-0e177ef8524041b39fbbc6ac61df8677
Source dataset
uspto-grants-2000_12
Patent number
US06166215

Reaction notes

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