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

HRID 1276655Notes

Reaction equation

HRID 1276655 reaction equation
[CH3:1][O:2][C:3](=[NH:8])[NH:4][N+:5]([O-:7])=[O:6].Cl.[Cl-].[Na+].N[CH2:13][C:14]1[S:18][C:17]([Cl:19])=[N:16][CH:15]=1.[OH-].[Na+]>O>[CH3:1][O:2][C:3](=[N:4][N+:5]([O-:7])=[O:6])[NH:8][CH2:13][C:14]1[S:18][C:17]([Cl:19])=[N:16][CH:15]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 101541292-Chloro-5-aminomethylthiazoleHCID 136196430O-methyl-N-nitroisourea

Product 1

HCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisoureaYield 64.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of O-methyl-N-nitroisourea (2.0 g, 0.0168 mol), 36% hydrochloric acid (1.5 ml), sodium chloride (8.0 g), and water (40 ml) was added 5-aminomethyl-2-chlorothiazole (2.5 g, 0.0168 mol) at 20° C. This mixture was adjusted to pH 7 with 30% aqueous solution of sodium hydroxide and stirred at room temperature for 8 hours, after which it was extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and concentrated to provide 2.7 g (64.1% yield) of O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea. M.p. 133-135° C.

Workup

  1. extractionafter which it was extracted with dichloromethane
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-586c4f12c8234bb5958fbc656779f070
Source dataset
uspto-grants-2000_12
Patent number
US06166215

Reaction notes

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