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

HRID 1276662Notes

Reaction equation

HRID 1276662 reaction equation
[NH2:1][CH2:2][C:3]1[S:7][C:6]([Cl:8])=[N:5][CH:4]=1.Cl.[CH3:10][O:11][C:12](=N)[NH:13][N+:14]([O-:16])=[O:15].[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

6

Reactant 4

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

Product 1

HCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisoureaYield 62.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(Aminomethyl)-2-chlorothiazole (7.43 g, 50.0 mmol) was dissolved in water (96 ml), and concentrated hydrochloric acid (4.22 ml, 50.0 mmol) was added. To this reaction mixture was added O-methyl-N-nitroisourea (7.19 g, 60.0 mmol), and adjusted to pH 6.7 with aqueous sodium hydroxide solution (0.5 N) using PH meter. After 20 hours of stirring at room temperature, maintaining pH 6.7, the resulting white crystals were collecte by filtration under reduced pressure, and washed with water. The washed crystals were dried under reduced pressure (80° C., 2 hours) to provide 7.85 g, (62.6% yield) of O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea.

Workup

  1. temperaturemaintaining pH 6.7
  2. filtrationthe resulting white crystals were collecte by filtration under reduced pressure
  3. washwashed with water
  4. customThe washed crystals were dried under reduced pressure (80° C., 2 hours)

Sources & evidence

ORD record
ord-77ce0d18341443b2b644c61150915ef0
Source dataset
uspto-grants-2000_12
Patent number
US06166215

Reaction notes

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