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

HRID 1276658Notes

Reaction equation

HRID 1276658 reaction equation
[CH3:1][O:2][C:3](=[NH:8])[NH:4][N+:5]([O-:7])=[O:6].[Cl-].[Na+].Cl(O)(=O)(=O)=O.N[CH2:17][C:18]1[S:22][C:21]([Cl:23])=[N:20][CH:19]=1.[OH-].[Na+]>O>[CH3:1][O:2][C:3](=[N:4][N+:5]([O-:7])=[O:6])[NH:8][CH2:17][C:18]1[S:22][C:21]([Cl:23])=[N:20][CH:19]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 101541292-Chloro-5-aminomethylthiazoleHCID 136196430O-methyl-N-nitroisourea

Product 1

HCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisoureaYield 62.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

O-methyl-N-nitroisourea (1.2 g, 0.01 mol) was added to water (30 ml) dissolving sodium chloride (4.7 g). Then, 70% perchloric acid (1.52 g, 0.0106 mol, 1.06 equivalents) was added, and 5-(aminomethyl)-2-chlorothiazole (1.49 g, 0.01 mol, 1.00 equivalent) was added at 24° C. The mixture was adjusted to pH 7 with 30% aqueous sodium hydroxide solution. After 24 hours of stirring at room temperature, the resulting crystals were collected by filtration to provide 1.55 g (62.2% yield) of O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea.

Workup

  1. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-cb74347b14f24ffa82e8632dba9e37bb
Source dataset
uspto-grants-2000_12
Patent number
US06166215

Reaction notes

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