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

HRID 613723Notes

Reaction equation

HRID 613723 reaction equation
[CH3:1][O:2][C:3](=[NH:8])[NH:4][N+:5]([O-:7])=[O:6].Cl.N[CH2:11][C:12]1[S:16][C:15]([Cl:17])=[N:14][CH:13]=1>O>[CH3:1][O:2][C:3](=[N:4][N+:5]([O-:7])=[O:6])[NH:8][CH2:11][C:12]1[S:16][C:15]([Cl:17])=[N:14][CH:13]=1

Participants

5

Reactant 3

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

Product 1

HCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisoureaYield 55.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of O-methyl-N-nitroisourea (3.0 g, 0.0252 mol), 36% hydrochloric acid (2.2 ml), and water (50 ml) was added 5-aminomethyl-2-chlorothiazole (93% purity, 4.4 g, 0.0275 mol) at 20° C. This mixture was stirred at room temperature for 6 hours and then extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and concentrated to provide 3.5 g (55.4% yield) of O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-738b691a1df64ada8c55e4a69bf44192
Source dataset
uspto-grants-1999_12
Patent number
US06008363

Reaction notes

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