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

HRID 1276660Notes

Reaction equation

HRID 1276660 reaction equation
[CH3:1][O:2][C:3](=[NH:8])[NH:4][N+:5]([O-:7])=[O:6].O.O.[Cl-].[Ca+2].[Cl-].Cl.N[CH2:16][C:17]1[S:21][C:20]([Cl:22])=[N:19][CH:18]=1.[OH-].[Na+]>O>[CH3:1][O:2][C:3](=[N:4][N+:5]([O-:7])=[O:6])[NH:8][CH2:16][C:17]1[S:21][C:20]([Cl:22])=[N:19][CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 6093260Calcium chloride, dihydrateHCID 101541292-Chloro-5-aminomethylthiazoleHCID 136196430O-methyl-N-nitroisourea

Product 1

HCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisoureaYield 59.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

O-methyl-N-nitroisourea (2.0 g, 0.0168 mol) was added to water (40 ml) dissolving calcium chloride dihydrate (8.0 g). Then, 36% hydrochloric acid (1.5 ml, 0.0176 mol, 1.05 equivalents) was added, and 5-(aminomethyl)-2-chlorothiazole (2.5 g, 0.0168 mol, 1.00 equivalent) was added at 24° C. The mixture was adjusted to pH 7 with 30% aqueous sodium hydroxide solution. After 19 hours of stirring at room temperature, the resulting crystals were collected by filtration to provide 2.48 g (59.1% 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-fceaa126511e44f29d3d02be36d181b2
Source dataset
uspto-grants-2000_12
Patent number
US06166215

Reaction notes

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