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

HRID 1276663Notes

Reaction equation

HRID 1276663 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]>[OH-].[Na+].O>[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 3

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

Product 1

HCID 136404632O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisoureaYield 64.6%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolvent

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) was added. The pH was 2.1 at this time. This reaction mixture was adjusted to pH 6.2 with aqueous sodium hydroxide solution (0.1 N, 4 ml, 0.40 mmol) using pH meter. Water (1 ml) was added to increase the whole volume to 20 ml. After 16 hours of stirring at room temperature (pH was 7.1 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 1.62 g (64.6% yield) of O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea.

Workup

  1. temperatureto increase the whole volume to 20 ml
  2. filtrationwere collected by filtration under reduced pressure
  3. washwashed with water
  4. customThe washed crystals were dried under reduced pressure (80° C., 2 hours)

Sources & evidence

ORD record
ord-e39b8cc4e99648798b6c5837442be4ce
Source dataset
uspto-grants-2000_12
Patent number
US06166215

Reaction notes

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