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

HRID 1276665Notes

Reaction equation

HRID 1276665 reaction equation
[NH2:1][CH2:2][C:3]1[S:7][C:6]([Cl:8])=[N:5][CH:4]=1.Cl.[CH3:10][O:11][C:12](=N)[NH:13][N+:14]([O-:16])=[O:15].[Cl-].[Na+]>[OH-].[Na+]>[CH3:10][O:11][C:12](=[N:13][N+:14]([O-:16])=[O:15])[NH:1][CH2:2][C:3]1[S:7][C:6]([Cl:8])=[N:5][CH:4]=1

Participants

6

Reactant 4

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

Product 1

HCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisoureaYield 69.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideCatalyst

Procedure

5-(Aminomethyl)-2-chlorothiazole (1.49 g, 10.0 mmol), was dissolved in diluted hydrochloric acid (15 ml, 10.0 mmol), and O-methyl-N-nitroisourea (1.31 g, 11.0 mmol) and sodium chloride (4.68 g, 80.0 mmol) were added. The pH was 1.9 at this time. This reaction mixture was adjusted to pH 6.2 with aqueous sodium hydroxide solution (0.1 N, 5.0 ml, 0.50 mmol) using pH meter. After 16 hours of stirring at room temperature (pH was 6.7 at this time), the resulting white crystals were collected by filtration under reduced pressure, and washed with water. The washed crystals were dried under reduced pressure (80° C., 2 hours) to provide 1.74 g (69.4% yield) of O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea.

Workup

  1. filtrationwere collected by filtration under reduced pressure
  2. washwashed with water
  3. customThe washed crystals were dried under reduced pressure (80° C., 2 hours)

Sources & evidence

ORD record
ord-313ce0edd5104ccd84ac7be341c8bd87
Source dataset
uspto-grants-2000_12
Patent number
US06166215

Reaction notes

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