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

HRID 613726Notes

Reaction equation

HRID 613726 reaction equation
[CH3:1][O:2][C:3](=[NH:8])[NH:4][N+:5]([O-:7])=[O:6].C(O)(=O)C.N[CH2:14][C:15]1[S:19][C:18]([Cl:20])=[N:17][CH:16]=1.[OH-].[Na+]>O>[CH3:1][O:2][C:3](=[N:4][N+:5]([O-:7])=[O:6])[NH:8][CH2:14][C:15]1[S:19][C:18]([Cl:20])=[N:17][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 101541292-Chloro-5-aminomethylthiazoleHCID 136196430O-methyl-N-nitroisourea

Product 1

HCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisoureaYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

O-methyl-N-nitroisourea (3.0 g, 0.0252 mol), acetic acid (1.5 ml, 0.0262 mol, 10.4 equivalents), and 5-(aminomethyl)-2-chlorothiazole (93% purity, 4.4 g, 0.0275 mol, 1.09 equivalents) were added to water (55 ml) in this order at 24° C. The reaction mixture was adjusted to pH 7 with 30% aqueous sodium hydroxide solution. The mixture was stirred at room temperature for 2 hours and then extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide 2.9 g (46.0% 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 under reduced pressure

Sources & evidence

ORD record
ord-c7a6f3442714478a8d48e5bfc1a3fa6b
Source dataset
uspto-grants-1999_12
Patent number
US06008363

Reaction notes

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